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Monkey D. Luffy (Pre-Timeskip) vs Superman (DCAU)

Luffy has the advantage in skill, AP by a bit, range, pain tolerance and Blunt Force Resistance.

Sups has flight, might last more in a fight and is probably more experienced.

But Luffy is too much for Sups in this case. I vote for the Rubber Band.
 
Luffy for the reasons Calaca outlined. Flight shouldn't be an issue given Luffy's abilities. Luffy would also be faster due to G2 putting him above the equalized speed.
 
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