I'm going Damon on this one. 9/10 I'd say that Damon get Deebo's cookies. Just going by what each has done to others. Deebo couldn't knock out Craig, and only partially knocked out Red. He was on the ground long enough for Smokey to say he got ktfo, but he got back up, and into the car with his dad. Whereas Damon knocked Money Mike out, and he stayed out until he threw water on him. "I like my fish squirming." Deebo is in danger of having his manhood taken. I would have sided with him, but going by what they've done to others, Damon has got him.
Damon never hit Money Mike. Mike fainted and hilariously so. I don't think Damon actually fought anyone; and in the scuffle with Mike(tho he wasn't actually trying to hurt Mike at that point, just undress him) Mike held him off long enough to get the upperhand. Deebo on the other hand sent Red FLYING!!!! That was funny as hell.
Damon had more "implied power"(Craig fought Deebo twice iirc but was terrified at the thought of tangling with Damon) but Deebo has actual fighting feats.
For some reason, Deebo appears as more of a badass to me than Damon. Damon is a nutjob who spent too much time in prison where Deebo seems to have embraced the gangster culture of his hood more perceivably.
And like stated above, Deebo actually has some fighting feats and lost to Craig only cause Ice Cube was going through a chosen one moment at that scene.