10 Villains Spider-Man Has NEVER Defeated
8. The Owl
Now sure, The Owl is more often associated with Daredevil, but Daredevil only lives a few blocks away from Peter so it makes sense that their villains like to mess with the other guy to see if they'd have more luck.
And The Owl has definitely had more luck messing with Peter than with Daredevil. Sure, they haven't tangled much, but when they have, Spidey finds himself oddly outmatched and often has to enlist other heroes to help out.
Spidey HAS won one time against The Owl, where he beat the crime lord to within an inch of his life, damn near killing him in the pages of Superior Spider-Man. However that doesn't really count, seeing as how that wasn't actually Peter, but instead Doc Ock in his body.
The Owl is not the most dangerous of Daredevil's rouges gallery, and yet the demented criminal has often eluded the webhead whenever he tries to take him down on his own.