Spiderman 2099 has his hand to hand skills. Diddy Kong is athletic, but he wouldn’t be able to last against Spiderman 2099. Diddy Kong lacks the power ups and power need to take down Spiderman 2099. Spiderman 2099 takes this win, but it has shown him that Diddy was tough…and almost won. Spiderman 2099 wins.