Nite Owl was breaking bones left and right and Ozy let him wail on his face for a good while without even drawing blood. I think he could take a few punches, assuming they actually manage to connect.
Ozy himself was breaking marble and concrete with his hits too, so I see him flurrying the heck out of Crossbones for the win
I forgot he took some from Nite Owl.
I don't know, Crossbones was jacking up Cap with those metal attachments for a little while and I see Cap as being much more durable than Ozy. Crossbones also took a stinger shock from Natasha right in the neck and acted like nothing even happened. He's fairly durable too.
Good fight either way.