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A badass gunslinger fights a cup

Okay.

Both seem to one shot with a good enough hit, as Mugman's smol building level beats Wall level Durability by far, and Roland's extremely high end Smol building level guns can do a number to him. Intangibility and Homing rounds can help to evade and hit the Gunslinger respectively, but considering Roland's extreme skill, he'll be able to easily find a pattern and exploit it. His instinctive reactions might even allow him to end the fight immediately by pulling his guns and capping Mugman before he can move.

Either way, Roland seems to win more times than not.
 
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