10 Times Spider-Man Has Been Outwitted
1. Spider-Man Fights Himself - Amazing Spider-Man #149
Top of the list for outwitting Spider-Man has to go to one of his most devious villains - Professor Miles Warren, AKA The Jackal. A former mentor of Peter Parker, the Jackal's revenge hit Peter mentally and physically. In the finale of the Delusion Conspiracy arc, written by Gerry Conway and pencilled by Ross Andru in 1975, Jackal uses Spider-Man's abilities against him - before ending their cat-and-mouse game with a lethal coup de grace.
Once the Jackal had succeeded in his plan to clone Gwen Stacy, his plan to get back at her "murderer" - who he thought was Spider-Man - started in a truly genius way - by earning Peter's trust. Since his Spider-Sense doesn't activate for trusted friends, Professor Warren was free to drug him into unconsciousness before growing a clone of him - forcing the two into a battle to the death, where both were perfectly evenly matched.
While one Spider-Man did manage to best the Jackal and free his hostages, the other was unfortunately killed - making the Jackal one of the only villains to murder Spider-Man. Between that and circumventing Peter's Spider-Sense without a single gadget, the Jackal definitely outwitted Spider-Man in this story.