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Drake from Uncharted 3.

VS

Jake Conway from Ride to Hell.

Round 1: Gunfight.
Both combatants gets a Colt 1911 and a Ithaca 37.

Round 2: Pure H2H.

The fight takes place in a Roman Colosseum with several containers to be used as cover.

Who wins and why?

LOL.

Nathan Drake destroys him.

Jake loses the first round due to his game's terrible aim system, but wins the 2nd round by doing a kick spam QTE.