10 Villains Spider-Man Has NEVER Defeated
3. Red Skull
Generally speaking, Spidey is not really prepared for someone as bad to the bone as Red Skull. Considering that the major players of Spider-Man's rogues gallery all share the consistent theme of good people twisted up by bad circumstances, it only makes sense that he wouldn't really know how to deal with a flat out evil Nazi.
Not to say that he tries to find some good in him, oh no, Spidey is all down for punching Nazis like any self respecting New Yorker. It's just that in all of their major encounters, Red Skull has managed to find some way to escape Spider-Man's clutches through clever trickery or overwhelming him by crossing lines that Spider-Man legit thought even he wouldn't cross.
The most important confrontation they've had is when Spider-Man takes on Red Skull to learn more about his parents in Amazing Spider-Man Annual #5. While he manages to get the answers he's looking for, he is unfortunately unable to take down Red Skull as well, and the Nazi escapes.
Considering that Red Skull doesn't have any overwhelming power to his name like other villains on this list, this may be the entry that will change in coming years. But until then, Red Skull remains undefeated by Spider-Man.