What If...? (1989) #58 — “The Day I Killed Spider-Man” (1994)

What If...? #58 explores a dark alternate reality in which the Punisher successfully kills Spider-Man, leading to a chain of events that reshapes the Marvel Universe 

The story begins with the Punisher holding a man at gunpoint, setting the stage for a flashback. In this timeline, the Punisher was hired by the Jackal to kill Spider-Man. His first attempt failed, but he learned about Spider-Man’s spider sense. Using that knowledge, he created a decoy Dr. Octopus filled with 30 pounds of plastic explosives. Spider-Man, unable to escape, is killed 

The Punisher later discovers Spider-Man was just a college student, realizing he was manipulated. Seeking revenge, he is hunted by most of New York’s crime-fighting heroes, forcing him into hiding. Eventually, Spider-Man’s enemies throw a celebratory party in his honor, which the Punisher attends and kills everyone present