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Deadpool would win easily, I mean... You shoot Deadpool in the head and he lives, he grows back, you know, he heals. You shoot Spider-Man in the head and that's it, he's fucking dead. Besides, what sport am I gonna do, web him to death?
I think it'll be a tough fight, but I feel like Deadpool might have more of an edge because he's not afraid to kill you. Where Spider-Man would be conscious of preserving your life and just tying you up, but Deadpool, he's trying to shoot you in Spider-Man interface.
Also, which Spider-Man are we talking about? Are we talking about Tom Holland's Spider-Man, or are we talking about Toby Maguire's Spider-Man? Toby Maguire's Spider-Man, he pushed someone out the window. Whereas Andrew Garfield, I don't know. Which Spider-Man are we talking about?