Sheldon Cooper vs Adrian Monk in a boxing match.
Both of them are in their prime during the shows they are part of. So say season 2 Sheldon is when he is physically his best well use that version.
Round 1 they fight as they are
Round 2 they get 6 months of training at the same boxing gym.
Round 3 they get the training but monk will be given info on his wife's murder if he wins and Sheldon will get a perfect 10 graded Amazing Fantasy 15 (Spider-man's first appearance)