Vulture I (Adrian Toomes)

File Photo

Black with Green irises


Hooked nose






175 lbs


Toomes is a brilliant electronics engineer with a great talent for invention.


Armed flight-suit housing electromagnetic anti-graviton generator allowing silent flight for up to 6 hours at a maximum altitude of 1,100 feet with precise maneuverability. The Vulture's top speed is 95m.p.h.


Old age.


No Innate Powers

Strength Level:

In costume: 700lbs, out of costume: Normal


Carries some form of plasma pistol & several grenades of unknown types.


United States of America

Created By:

Stan Lee, Steve Ditko

Current Groups:

Sinister Six IV (Electro, Mysterio, Sandman, Kraven II)

Current Occupation:

Professional Criminal

Dual Identity:

Publicly known


Masters of Science degree in electrical engineering

Former Bases:

Las Vegas, Atlantic City

Former Groups:

Sinister Six I (Doctor Octopus, Electro, Kraven, Mysterio, Sandman), Sinister Six II (Doctor Octopus, Electro, Hobgoblin II, Mysterio, Sandman)

Former Occupation:

Electrical Engineer

Known Allies:

Electro, Mysterio, Hobgoblin II (deceased), Shocker, Scorpia, Beetle, Doctor Octopus, Kraven (deceased), Sandman, Owl, Chameleon (deceased), Venom

Known Relatives:

Malachi Toomes (nephew, deceased); unnamed son; Ramona (daughter in law); unnamed son; Marcus (older brother)

Legal Status:

Criminal record in U.S.

Major Enemies:

Spider-Man, Gregory Bestman, Blackie Drago, Mr. Morgan, The Vulturians, Daredevil, Scarlet Spider (deceased), Kaine, New Mutants, Prowler, Hobgoblin I

Marital Status:


Place of Birth:

Staten Island, New York

Real Name:

Adrian Toomes

Usual Bases:

New York City



Not much is known about Adrian Toomes's life before he became the Vulture. His parents died when he was young and he was raised by his older brother, Marcus. At some point Marcus was involved in a motorcycle accident, leaving him paralyzed from the neck down. Marcus gave up on life and begged Adrian to push his wheelchair in to the ocean. Adrian refused to kill his brother, prompting Marcus to tell him that all humans are just animals, and that they were both weak, but that Adrian was weaker because he refused to admit it. (Friendly Neighborhood Spider-Man #15)

Toomes's career as a criminal began when he discovered his then partner Gregory Bestman (in the engineering firm of Bestman & Toomes) had been cheating him out of his share of the profits. The elderly Toomes confronted Bestman and in doing so discovered that he, Toomes, had somehow gained incredible strength. Toomes had already begun work on his now infamous electromagnetic flying harness and discovered that exposure to its unique radiation had granted him super-human strength. Bestman threw Toomes out of the company. Enraged, the elderly inventor took his creation with him, to perfect it as a weapon against his former partner. Dubbing himself the Vulture, Toomes ransacked his former company, feeling that the money was rightfully his. (Amazing Spider-Man #241)

Intoxicated with his new found power and the ease with which he committed his crime, the Vulture went on a wild crime spree, daring the police to catch him. At J Jonah Jameson's NOW magazine building, he threw a rock through a window with a message threatening to steal one million dollars worth of diamonds from a Park Avenue jewelry exchange. He came across Spider-Man as the teenager was fumbling with his camera to get a picture of the winged menace and took him by surprise. Spidey never knew what hit him after the old man hit him from behind and dumped his unconscious body in a nearby water tower. He soon made good on his promise to steal the diamonds, this time from a sewer tunnel instead of from the sky. He escaped through the sewers and out a subway tunnel before heading back to his farmhouse silo on Staten Island. Spider-Man had since escaped from the water tower and created a device that interfered with Toomes' flying harness. The gadget successfully forced the Vulture to land, where he was webbed by the wall crawler and taken by the police. (Amazing Spider-Man #2)

"The Return of the Vulture"

Adrian acted the part of the model prisoner to get more privileges, and the warden made him a trustee and gave him access to the prison shop. Little did anyone know, but he was building another, albeit less powerful, flying harness to escape. After building a new harness, he was flying circles around police helicopters and back to robbing jewelry stores. Spider-Man was soon on his trail and ready to use his anti magnetism device again. Toomes had expected that, and had remade his harness to function despite Spidey's gadget. He feigned falling from the sky but as the web swinger got his camera ready, Vulture doubled back and hit him from below. The old man pummeled Spider-Man and then dropped him. Spidey missed catching a surface with his webline and hit a rooftop hard, spraining his arm. Toomes next taget was the Daily Bugle and the employee pay checks. Jameson begged Vulture not to take them and as they argued, Peter got into costume despite the pain in his arm. The fight raged through the Daily Bugle and then over the skies of New York until Spidey webbed his wings together. Spider-Man spun a web parachute and tied it to the crook, letting it carry him to the street. (Amazing Spider-Man #7)

"The Sinister Six"

Along with Kraven the Hunter, Electro, Mysterio and Sandman, Toomes was a founding member of the Sinister Six, which was led by Doctor Octopus. The Six kidnapped Aunt May and Betty Brant in order to draw out Spider-Man. Each villain took on Spider-Man mano a mano, with the battlegrounds suited to the crook's strengths. Vulture met Spider-Man at the top of the Empire State Building and forced the web-slinger to throw away his web shooters. Despite the loss of his most versatile weapon, Spidey's amazing agility was enough to overwhelm Toomes, and Spider-Man went on to face the next challenger. (Amazing Spider-Man Annual #1)

"The Wings of the Vulture"

Back in prison, Toomes suffered an accident in the work shop and believed he was near death. In the prison infirmary he demanded to see his cellmate, Blackie Drago, and give him an important message. Drago had pestered Toomes for months, wanting to know where he kept his spare wings. Believing himself close to death, Adrian agreed to tell Blackie where they had been hidden on the condition that he kill Spider-Man. Immediately after being told that the wings were buried right outside the prison walls, a gloating Drago told Toomes that he had arranged the "accident" in the workshop to make the old man talk. Drago soon escaped with the flying harness, leaving Toomes to seethe with rage over the betrayal. (Amazing Spider-Man #48)

"Wings in the Night"

Drago was eventually defeated in a three way fight with Spider-Man and Kraven and sent back to prison. Meanwhile, Toomes had pulled through and become healthy enough to escape prison and become the Vulture again. His first crime was to break into the museum that held the wings that had been taken by Drago. He returned to prison and broke out Blackie, ordering him to put the wings on. After getting clear of the guards guns, Blackie demanded to know how Adrian was still alive. Toomes explained that he used the confusion in the prison caused by Drago's escape to escape himself. He had overpowered a guard and used his uniform to disguise himself. In the coming months, Adrian rebuilt his wings and planned his revenge. He challenged Drago to fight him in the skies over New York, to prove who was the real Vulture. During the fight, the two collided into a balcony and nearly knocked a young boy to his death. Spider-Man saved the day and after Toomes defeated Drago, he turned his attention to the web head. (Amazing Spider-Man #63)

"The Vulture's Prey"

Spider-Man held his own against the Vulture, but he had hurt his arm after falling to a rooftop in the rain and catching the boy had made it worse. Spidey had webbed the Vulture's legs but the crook swung him around midair, nearly missing Jonah Jameson and Robbie Robertson, who were watching from the Bugle's roof. Vulture smashed into the Bugle sign and a piece of concrete fell to the rooftop, nearly crushing Robbie. In a rage, Jonah grabbed Spider-Man and held him so Vulture could take him out but the web slinger was able to flip him over and still avoid Toomes' attack. Spidey took the time to attend to Robbie, who didnt seem to have any broken bones. the fight with Vulture resumed but the beating Spider-Man took , combined with the injured arm, caused him to fall to the street. He managed to land on a web cushion and break his fall but he was soon confronted by the Vulture. Spidey managed to damage Toomes electro magnetic harness, causing the criminal to fly away before his power source died. (Amazing Spider-Man #64)

"The Dark Wings of Death"

The third Vulture was a professor at Empire State University named Dr. Clifton Shallot. He was a professor of bio-mutation and became obsessed with killing anyone that knew about his secret experiments. (Amazing Spider-Man #127 and #128)


Toomes laid low for quite a while, anonymously working in a repair shop, all the while tinkering with his harness and making improvements. A local mobster named Morgan had tried to muscle him for protection money, and Vulture replied by dumping his goon into the Hudson River. Vulture again humiliated Morgan when he came to talk to the old man, and left the mobster hanging from a lamp post. As Vulture had humiliated Morgan, he would humiliate Toomes. Vulture struck next by taking hostages every fifteen minutes until Spider-Man arrived. Morgan watched the news on TV and hired the Hitman to kill Spider-Man before Vulture could do it. Hitman finds Vulture standing over an electrocuted Spidey and Vulture fights to protect his that he can kill him. (Spectacular Spider-Man #4)

Spider-Man is surprised at Hitman's speed and shooting accuracy and he escapes out a window. Vulture is also surprised and forced to flee after he gets a face full of mace. A tracer had been placed on Vulture's back, and Hitman followed him to goad him into another fight with his modified weapons. Vulture followed him to Peter's neighborhood, because Hitman had also placed a tracer on Spidey. The fight drew out the web swinger and the fight moved to Central Park. Vulch and Spidey battled on top of a construction crane and Spidey feigned helplessness as he dangled from a webline. Vulture dove at his enemy as the Hitman took a careful shot at the hero. Spidey beat them both by catching Vulture in his legs and turning him around in time for the bullet to destroy Toomes' power pack. Hitman fled the scene as the contract was to kill Spider-Man and steal Toomes revenge. That was now impossible, as Toomes was helpless. (Spectacular Spider-Man #5)

"The Vengeance Gambit"

Toomes was especially ambitious when he tried to take over the Kingpin's empire after Fisk "retired" from organized crime. Using his nephew, Malachi Toomes, as an intermediary with the squabbling, remaining crime bosses, Vulture hoped to rule the New York mafia. Through several tests of loyalty, Toomes used the mafia to kill potential rivals. After "Black Alfred" found out he had been used by the Vulture, he swore revenge and shot Malachi. His nephew's death badly upset Vulture. (Spectacular Spider-Man #44)

"Let Fly These Aged Wings"

Adrian was soon captured again, in physical therapy after many of his bones had been broken. He would only be in therapy long enough to get well, and would then be moved to a federal prison. An orderly left Toomes alone to get his information and while alone, Adrian met another elderly patient, Nathan Lubensky. Adrian told the friendly man that he felt like a useless old fool without family or friends. Nathan disagreed, telling Toomes that he would be his friend and that age was only a state of mind. After Nathan left, Adrian decided that he wasnt dead yet and that he was still capable. He created a new harness after tinkering with electronics in the therapy room and was soon crashing out of the window to freedom. He was soon back to robbing jewelry stores and armored trucks. After his last robbery, he went back to his nursing home, which he considered to be the perfect hideout. Adrian was soon playing poker with Nathan and his friends when Peter Parker arrived to see May. Peter instantly recognized Toomes and Adrian saw the look of stunned recognition. Toomes used a cover story, and a gun hidden in his coat, to convince Peter to come back to his room and see his photographs. As soon as they arrived, Toomes hit Peter over the head with the gun and tied him up. He changed into the Vulture and was going to drop Peter from 10,000 feet when May knocked on his door, looking for her nephew. Adrian told her he left and after a confused May went away, he turned back to Peter and found Spider-Man waiting for him. The fight crashed from room to room in the retirement home, eventually leading back to the rec room. Vulture tried to take a hostage and found that he had grabbed Nathan. He refused to hurt his new friend, but did shove him in his wheelchair back at Spider-Man and used the distraction to escape. Spidey was unable to follow as he was surrounded by fragile elderly residents that wanted to thank him. (Amazing Spider-Man #224)

"High Stakes"

Vulture was trying to peddle trick dice in Atlantic City. The dice was made of a plastic that the casino could control with ultra sonic waves. He was turned down by a gangster and got revenge later by smashing up his casino. Naturally Peter was there with Aunt May and his spider sense warned him of danger. Peter changed into Spidey and went after Vulture, but the Hobgoblin (probably Ned Leeds) showed up. This casino's owner was in league with the Rose and Hobgoblin was his enforcer. Vulture had no interest in taking on both Spider-Man and Hobgoblin and fled. (Web of Spider-Man #24)

"Death From Above"

Toomes later set his eyes on revenge on the Las Vegas mafia, who he felt had cheated and humiliated him in Atlantic City. His target was Morris "The Snake" Diamond, a casino owner. Diamond laughed in Toomes face and later ordered the death of Randall Reese, the inventor of the plastic, who was traveling with Toomes. Diamond's boys had also stolen Reese's journals, which detailed how to make the plastic. Vulture managed to crash the plane to New York that both Diamond and Peter Parker were traveling on, stranding the passengers in the desert. Spider-Man managed to capture the Vulture and the Diamond gang, with the help of flight attendant/Central Intelligence Division agent Sara Glenville. (Web of Spider-Man #45)

"The Return of the Sinister Six"

"The Revenge of the Sinister Six"

"Funeral Arrangements"

In one of those comic book coincidences, Lubensky had been a friend of Toomes and was the fiance of Peter's Aunt May. Wrecked by guilt over causing his friends death, Adrian went to Aunt May to beg her forgiveness. In a rage, May slapped Vulture and forbade him from ever coming to her house again. Peter stayed the night with May to keep watch over her, and when Adrian returned, he took off with Peter when the police arrived. Toomes swore to Peter that he didn't mean to kill Nathan and Peter began to believe that Adrian was truly sorry for his crimes, until he saw the body of Gregory Bestman on the floor of Vulture's hideout. Peter managed to escape and come back as Spider-Man, defeated Vulture and brought him back to May to force him to apologize. She couldn't do that, and could only say that forgiveness was between Toomes and God.


Toomes's desperation for a cure led him to team with the Chameleon, who was in the midst of a plan, concocted by Harry Osborn right before his death, to avenge Kraven's death (enough villain overlap for you?). Over the course of these invents the Vulture found himself rejuvenated, the cancer gone from his system and his youth restored. As a result Toomes updated his costume to a suit of battle-armor, complete with a host of new weapons. The "new" Vulture proven to be even more short-tempered, cruel and dangerous than the "old," as his youth depended on his ability to drain the vitality out of others.

"Back From the Edge"

Vulture tried committing mass murder with an experimental virus that he stole from the military. He liked being his stronger, youthful self and couldn't bear anyone remembering what a weak old man he had been. With the help of the Owl, Vulture was going to spread the virus all over New York via vultures, eagles and other birds. They were defeated by Spider-Man and Daredevil, but not before one of the birds infected Peter with the virus. Peter only survived after Doctor Octopus created an antidote.

"Unholy Alliances"

He joined the Sinister Seven (Jason Macendale, Electro, Scorpia, Shocker, Mysterio and Beetle) in their attempt to kill the villain-slaying Kaine.

"Powerless and Responsibility"

He also fought the second Prowler, around this time. Toomes had already fought and badly hurt Hobie Brown, the original Prowler and attacked the third Prowler (Rick Lawson) thinking that it was Brown. He gutted the new Prowler, who was a hospital attendant for Brown and had stolen his costumed identity. Spidey took the injured man to the hospital, where he survived. Toomes's rejuvenation didn't last long. During a battle with Spider-Man, he was attacked by David Kalen who somehow sucked the youth from him. Easy come, easy go. (Sensational Spider-Man #18)

"Identity Crisis"

Toomes soon fought Peter after he assumed the Hornet identity. Norman Osborn had framed Spider-Man for assault and put a bounty on his head, so everyone with a gun came after the web swinger. "Hornet" had claimed on TV that New York didn't have to worry about Spider-Man any more and an enraged Vulture assumed that Hornet had claimed to have killed his foe. Vulture went after Hornet and nearly defeated him due to Toomes greater experience in flying, until Hornet crashed him into a billboard. (Sensational Spider-Man #28)

"Snow Day"

Spidey stumbled across Toomes one snowy day after the crook held up a jewelry store. Toomes assumed that Spidey had been following him and tried ro kill him, but Spodey managed to take back the gems. Vulture challenged Spider-Man to a final fight, mano a mano at the site of their first fight. Spidey waits at the top of the Empire State Building through a snow storm, but wonders why Vulture is late. Its actually because their first fight was st the Chrystler Building. Toomes finds Spider-Man and pulls an uzi on him, telling him that he lied about going mano a mano. Spidey lied too, and the Human Torch arrives, frying Vultures wings. Spidey punches Vulture in the face and he goes spiraling down into a snow bank as Spider-Man and Torch laugh. (Peter Parker: Spider-Man vol 2 #37)

"Down Among the Dead Men"

As much as he would deny it, Vulture does have a kind side. He would consider it a weakness, but not only did he ask May for forgiveness, he also has stolen to provide for his young grandson. He didn't even know he had a grandchild until his daughter in law brought him in to Riker's Island to meet Adrian. Toomes's son was in jail for armed robbery, the boy had been diagnosed with leukemia and his mother had no way to pay for the treatments. With the aid of Electro, he stole $20 million but the money was lost in a fight with Spider-Man. Peter managed to get $5 million to the boy's mother.

"Taking Wing"

After Peter revealed his ID on live TV during the Superhuman Registration Act, Toomes attacked Deborah Whitman, who had written a tell all book about her past with Spider-Man. Attacking Deb drew out Peter and Toomes suffered a stroke in mid air during the battle. Afterward, Vulture claimed that he's rather die than be saved by a compassionate weakling like Spider-Man. In a rage, Peter began suffocating Toomes in his hospital bed with a pillow. He stopped after Toomes struggled. Peter told him that for a man who said he wanted to die, he definitely fought to live. (Friendly Neighborhood Spider-Man #16)

Toomes went through a forced transformation after Stegron brought a crystal from the arctic, bringing out the inner animal of everyone in New York. Like a real vulture, Toomes began murdering and eating the corpses of random people. Lately, he was kidnapped by a former Sinister Six member: Alyosha Kravinoff. Alyosha was hunting animal themed super villains and was stopped by the Punisher.


When a new, mutated Vulture came on the scene, Spidey paid a visit to his old friend in prison. While Adrian had only heard rumors, he gave Spider-Man a clue that the red costumed Vulture was a former mafia hitman named James Natale. Natale was forced to undergo experiments to be deadlier and Adrian hoped he killed Spidey. (Amazing Spider-Man #594)

"Great Heights"

A while later, a free Toomes was using teenage delinquents as surrogate Vultures. He didn't trust them to give him his share of the loot that they stole, so he kept track of their weight before and after a heist. He knew down to the ounce how much each teen was to steal and if they were so much as two coins over the limit, he would turn off their magnetized wings in mid-air. This had happened several times, and the apparent teen suicides drew the attention of Spider-Man and Carlie Cooper. Spidey suspected that Toomes was behind the deaths when one of the dead criminal's body piercings was found to be magnetized. Further evidence led Peter and Carlie to a club called the Wake. (A Wake is a flock of vultures.) The teens were captured and Toomes escaped after he tossed a water tower at Carlie. (Amazing Spider-Man #673)

"My Own Worst Enemy"

Adrian didn't fare as well when he next faced Spider-Man (Octavius). He was using children to steal back jewelry from The Wake. His electromagnetic signature used by his flying device was used by Spider-Man to track him back to his hideout. Children were easy to use as henchmen, as all they asked for were game tokens and pizza. Spider-Man became enraged when he learned that kids were being used, as it reminded him of his childhood abuse at the hands of his father. Toomes fled in the face of the strangely furious Spider-Man but was beaten after being blinded by and crashing into the spider-signal used by mayor Jameson, badly cutting and burning Toomes in the process. (Superior Spider-Man #3)

"No Escape"

The Vulture was blinded after the battle and was incarcerated at The Raft in a medical ward with the Scorpion and Boomerang, both of whom had also been badly injured by the new webhead. At the same time, Alistaire Smythe was about to be executed and Spider-Man was there to make sure he didn't escape. Smythe did try to avoid his fate with tiny robots. Spider-Man had expected this and had his own tiny robots at the ready. As Spider-Man attempted to apprehend the escaping mad scientist, Alistaire's robots arrived at the medical ward and cured Toomes of his blindness, as well as freeing Scorpion and Boomerang. In return, they were tasked to kill the wall crawler. (Superior Spider-Man #11)

Toomes and the others soon began to over power the wall crawler, until Smythe gave them new orders to attack Jonah Jameson and the other hostages (Norah Winters, Glory Grant, the head of security of The Raft, Smythe's lawyer and a priest) which Toomes set out to do while Scorpion went after Jameson and Boomerang stayed with Spider-Man. (Superior Spider-Man #12) Arriving at the hostage site, Vulture found a weakness in the force field they were protected by and began to power it down when the people inside began to offer deals with him. Grant claimed she could spin the story so he was the hero of the ordeal. One of the D.A.s promised leniency and Smythe's lawyer said he could say that Smythe's technology made Toomes act against his will. He considered all of the offers but was soon powerless after Spider-Man killed Smythe, making all his upgrades to the other criminals power down. Toomes was shot for good measure by The Raft's head of security. (Superior Spider-Man #13)

"The Superior Six"

Vulture was soon in the custody of Spider-Man, who implanted a mind control chip and forced him to join his Superior Six. The new Six were forced to act as heroic vigilantes under Spider-Man's mind control. Their first mission was to protect Alchemax, the new corporation of Liz Allan, which was under attack from The Wrecking Crew. The Wrecking Crew got away but the particle engine was saved, only to be taken back to Parker Industries by Spider-Man. (Superior Spider-Man Team Up #5)

Vulture and the rest of the "Superior Six" later faced off against Whirlwind, who was bait for the rest of the Masters of Evil to attack the Six. Meanwhile, the boss of the Masters, Lightmaster, was stealing the engine from Parker Industries. The Six were joined by Sun Girl, who eventually set off the device on Spider-Man's orders. This was a mistake, as it defeated Lightmaster and the Masters of Evil, but also made Sandman into a giant and erased the mind control used on the Six. (Superior Spider-Man Team Up #6)

Vulture and Electro took part in torturing Lightmaster to force him to tell how the particle engine worked. When he didnt talk, Vulture dropped him from the air but he was caught by Sun Girl, his daughter. Vulture and Mysterion tried to kill her but were beaten by the girl. (Superior Spider-Man Team Up #7)

"Project Twilight"

Toomes was hired by the Tinkerer to kidnap his brother, Hophni Mason, and destroy his lab. Spider-Man and ex-S.H.E.I.L.D. agent Teresa Durand arrived just as Vulture was about to blow the lab apart. (Peter Parker: The Spectacular Spider-Man #4 vol. 3)

Vulture escaped with Hophni but was hit with a webline by Durand, who was carried away by the crook. While she dealt with Toomes, Spider-Man tried to smother as many of the bombs with webbing as he could. The building was still leveled by explosions and Spidey managed to hold up the ceiling before it crushed him and the boy named Uatu. Vulture saw he was dragging Durand with him and before he could cut her away, she pulled Hophni away with another web. Her own wings saved her and as Vulture came back to finish them off, he was trounced by Spider-Man. He managed to escape before Spidey could capture him. (Peter Parker: The Spectacular Spider-Man #5 vol. 3)

"Most Wanted"

Vulture next attacked Peter and Teresa as they tried fleeing New York for San Francisco. He blew up several cars on the bridge they were on to draw them out, and Spidey quickly taxkled him. Teresa was grabbed by Whiplash and thrown into the windshield of a truck. Vulture explained that Tinkerer had helped them, so they were returning the favor. Whiplash said that information was hidden inside Teresa, but they didnt need her to be alive to get it. Spidey was about to throw a car at Whiplash but was cut by one of Vulture's knives. He complained that he wanted it over with, because he was tired of being in debt to Tinkerer for the new wings. The wings were then ripped apart by Black Panther, who arrived in the knick of time. He kicked Vulture into the river beneath the bridge, who surfaced a time later and made a calll to Tinkerer. Black Panther was a problem, and suggested Tinkerer send everyone. (Peter Parker: The Spectacular Spider-Man # 298)


Cover Date Appearance Information
Oct 1999 App: Guts & Glory
May 1963 1st: Amazing Spider-Man (Vol. 1) #2 (Story 1)
  First encountered Spider-Man during jewelry heist
Dec 1963 App: Amazing Spider-Man (Vol. 1) #7
  Modified harness, attemped to rob the Daily Bugle payroll
Year 1964 App: Amazing Spider-Man (Vol. 1) Annual #1 (Story 1)
  Joined original Sinister Six
Jan 1996 App: Untold Tales of Spider-Man #5
Apr 1997 App: Untold Tales of Spider-Man #20
Nov 1964 App: Amazing Spider-Man (Vol. 1) #18
May 1967 App: Amazing Spider-Man (Vol. 1) #48
  Believed self dying in prison, revealed location of extra Vulture outfit to cellmate Blackie Dargo who became second Vulture
Aug 1968 App: Amazing Spider-Man (Vol. 1) #63
  Toomes defeated Dargo
Sep 1968 App: Amazing Spider-Man (Vol. 1) #64
  Defeated Spider-Man in battle
Mar 1977 App: Spectacular Spider-Man (Vol. 1) #4
  Humiliated racketeering mobster, Mr. Morgan, for trying to steal the Vulture's revenge by hiring the Hitman to kill Spidey
Apr 1977 App: Spectacular Spider-Man (Vol. 1) #5
Jul 1980 App: Spectacular Spider-Man (Vol. 1) #44
  Arranged murder of New York's top mobsters to become crimelord, battled Spidey
Aug 1980 App: Spectacular Spider-Man (Vol. 1) #45
Jul 1981 App: Spectacular Spider-Man (Vol. 1) #56
Jan 1982 App: Amazing Spider-Man (Vol. 1) #224
  Escaped prison, battled Spidey
May 1983 App: Amazing Spider-Man (Vol. 1) #240
  Came out of retirement to attack Gregory Bestman. Origin told.
Jun 1983 App: Amazing Spider-Man (Vol. 1) #241
Jun 1985 App: Web of Spider-Man (Vol. 1) #3
  Confronted Vulturians, a group of youths who stole his designs
Date TBD App: Daredevil (Vol.1) #225
Jan 1986 App: Secret Wars II #7
Feb 1987 App: Web of Spider-Man (Vol. 1) #23
  Atlantic City, fights Hobgoblin
Mar 1987 App: Web of Spider-Man (Vol. 1) #24
  Las Vegas
Nov 1987 App: Power Pack #33
Dec 1988 App: Web of Spider-Man (Vol. 1) #45
Date TBD App: New Mutants #83
  Confronted mutants Rusty Collins & Skids in an attempt to release Nitro
Date TBD App: New Mutants #84
Date TBD App: New Mutants #85
Date TBD App: New Mutants #86
Aug 1990 App: Amazing Spider-Man (Vol. 1) #336
  Rejoined Sinister Six, killed Nathan Lubensky, battled Spider-Man
Aug 1990 App: Amazing Spider-Man (Vol. 1) #337
Sep 1990 App: Amazing Spider-Man (Vol. 1) #338
Sep 1990 App: Amazing Spider-Man (Vol. 1) #339
Jan 1992 App: Spider-Man (Vol. 1) #18
  w/ Sinister Six, battled Spider-Man, Fantastic Four, Ghost-Rider, the Hulk, & Nova
Feb 1992 App: Spider-Man (Vol. 1) #19 (Story 1)
Mar 1992 App: Spider-Man (Vol. 1) #20 (Story 1)
Apr 1992 App: Spider-Man (Vol. 1) #21
May 1992 App: Spider-Man (Vol. 1) #22
Jun 1992 App: Spider-Man (Vol. 1) #23
Mar 1992 App: Spectacular Spider-Man (Vol. 1) #186
  Discovers has cancer, decides to kill all his enemies
Apr 1992 App: Spectacular Spider-Man (Vol. 1) #187
May 1992 App: Spectacular Spider-Man (Vol. 1) #188
Feb 1994 App: Amazing Spider-Man (Vol. 1) #386
  Aided Chameleon in revenge on Spider-Man, youth and health restored, donned redesigned costume and weapons
Mar 1994 App: Amazing Spider-Man (Vol. 1) #387
Apr 1994 App: Amazing Spider-Man (Vol. 1) #388 (Story 1)
Dec 1994 App: Amazing Spider-Man (Vol. 1) #396
  w/ Owl, attempted poisoning of all his enemies, battled Spider-Man & Daredevil, poisoned Spider-Man
Dec 1994 App: Spectacular Spider-Man (Vol. 1) #219
Mar 1995 App: Spider-Man: Funeral for an Octopus #1
  w/ Electro, Hobgoblin, & Mysterio, attemped theft of Dr. Ock's arms, battled Spider-Man, Scarlet-Spider, & Kaine
Apr 1995 App: Spider-Man: Funeral for an Octopus #2
May 1995 App: Spider-Man Unlimited #9
  Formed Sinister Seven to kill Kaine
Nov 1994 App: Prowler #1
Sep 1995 App: Spider-Man (Vol. 1) #62
Sep 1995 App: Spider-Man Unlimited #10
  Sinister Seven again
May 1997 App: Sensational Spider-Man (Vol. 1) #16 (Story 1)
Jun 1997 App: Sensational Spider-Man (Vol. 1) #17 (Story 1)
Aug 1997 App: Sensational Spider-Man (Vol. 1) #18
Apr 1998 App: Sensational Spider-Man (Vol. 1) #26
May 1998 App: Sensational Spider-Man (Vol. 1) #27
Jun 1998 App: Sensational Spider-Man (Vol. 1) #28
Dec 1999 App: Amazing Spider-Man (Vol. 2) #12 (Story 1)
Dec 1999 App: Peter Parker: Spider-Man (Vol. 2) #12
Mar 2000 App: Webspinners Tales of Spider-Man #15
  Blacked out parts of New York to perform burglaries
Apr 2000 App: Webspinners Tales of Spider-Man #16
Apr 2002 App: Spider-Man Tangled Web #11
Jan 2002 App: Peter Parker: Spider-Man (Vol. 2) #37
Jun 2002 App: Spider-Man Tangled Web #13
May 2004 App: The Pulse #2
Jul 2004 App: Marvel Knights: Spider-Man #2
Aug 2004 App: Marvel Knights: Spider-Man #3
Sep 2004 App: Marvel Knights: Spider-Man #4
Mar 2005 App: Marvel Knights: Spider-Man #10
Apr 2005 App: Marvel Knights: Spider-Man #11
Apr 2006 FB: Friendly Neighborhood Spider-Man #5
Apr 2006 App: Sensational Spider-Man (Vol. 2) #23
Jan 2007 App: Friendly Neighborhood Spider-Man #14
Feb 2007 App: Friendly Neighborhood Spider-Man #15
Mar 2007 App: Friendly Neighborhood Spider-Man #16
Jun 2009 App: Amazing Spider-Man (Vol. 1) #594
Apr 2010 App: Web of Spider-Man (Vol. 2) #5 (Story 1)
Jan 2012 App: Amazing Spider-Man (Vol. 1) #674
Feb 2012 App: Amazing Spider-Man (Vol. 1) #675
Mar 2013 BTS: Superior Spider-Man #2
Apr 2013 App: Superior Spider-Man #3
Aug 2013 App: Superior Spider-Man #11
Aug 2013 App: Superior Spider-Man #12
Sep 2013 App: Superior Spider-Man #13

Thanks To

 The assistance of the Marvel Chronology Project is gratefully acknowledged.

 Some of the above information is extracted from the various versions of the Official Handbook to the Marvel Universe and the more recent Marvel Encyclopaedias.