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Daredevil and Kingpin vs Captain America and Red Skull
This is just a brawl, no weapons, no shield.

Team one is tough as heck but Steve seals the deal.

Yeah, I think it would be a tough fight, but Captain America would probably pull through and win.

Could go either way. Fisk has beaten Red Skull in the past, and did it convincingly enough, that I am comfortable saying that he would again.

This would depend on how long it takes Fisk to win against the Red Skull, because for some odd reason, I see Daredevil taking longer to go down if he fought Captain America, as opposed to if Kingpin fought the Red Skull. I see a possible double team in more cases than not.