For all rounds, John has a High Table armor's helmet on top of his usual bulletproof suits, to compensate for the fact that Dex's Daredevil suit has a bullet-resistant helmet.
Round 1: Standard fight. John has his gun, Poindexter has his billy clubs (or a gun if the clubs cannot damage John).
Round 2: Neither of them starts with weapons. However they are each at one end of an office supplies store, at night so that there is nobody else.
Bonus round: John vs Matt, H2H. Matt has the Daredevil armor, but is physically his first half of Season 3 self (let's say around the first Bullseye fight).