Round 1: Random Encounter Round 2: Morals off for Peter
STI
StiltmanFTWCBvF
One of Parker's greatest enemies is a watered down version of Omega Red.
Red eats him.
STO
StoicAvenger
I can't see Spidey having a chance here, unless he kept his distance and webbed Omega Red up (If that would even work). He may also be able to win in certain environments that allow him to toss large objects at him, but up close his chances are slim.
KIN
KingD19Shai-Gen's Enigmatic Wong
Between Arkady's armor, his own durability, HF, strength, and his tendrils, that wouldn't even help much.
STO
StoicAvenger
Spidey has overcome some pretty steep odds, so I wouldn't be surprised if he did win.