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Round 1: Gunfight, Ash gets his boomstick, Castle gets whatever handgun he normally uses, battle takes place at the cabin from Evil Dead 1 for this fight, plenty of trees to use for cover.

Round 2: Fist Fight, Ash gets both his hands.

Round 3: Ash gets his metal hand, Frank gets brass knuckles.

Round 4: Anything goes, Ash has his chainsaw arm, but no boomstick, Castle gets a sledgehammer, battle takes place at the construction yard from Netflix Punisher Season 1, I just feel the setting fits this fight well. Remember anything goes so environmental surroundings and the possibility of winning after losing their weapon still counts.

If you think Castle stomps the H2H rounds, replace normal Ash with Deadite Ash from Evil Dead 2.

Ash gets his experience from Evil Dead 1 & 2 all the way to the end of Army of Darkness.

Frank gets his experience from The Punisher Netflix series and DareDevil series.

bump

Castle should win them all as he's the better fighter and combat trained, but Ash is at times Looney Tunes level, so considering that, I'd give all three rounds to Ash.