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I believe Chop Chop Master Onion wins via having more hax and a better arsenal. And while it is pretty even across the board, Chop Chop is a karate master while All Might's really noted as experienced in hand to hand so Chop Chop would have the advantage in a close encounter.
 
All Might has an advantage fighting from a distance via shock waves, where as the winds that Chop Chop can create aren't that powerful (and do no real damage for that matter). If All Might see's that Chop Chop is too dangerous to fight up close, he could instead rely on using his environment using pieces of the battlefield as throwing weapons (such as large chunks of the ground) or again; throw shock waves at his opponent.

Plus once Chop Chop becomes giant sized, I think he'd just end up being a bigger target for All Might. Plus at such a size, All Might would be too small to grapple/fight properly.

BUT since Chop Chop is aware of what All Might can do in this scenario he'd likely have this information in mind and do what he can to get in close and take him down at quickly as possible. He's also shown the ability to grapple and contort his body, so once he gets ahold of All Might he probrably won't let go.

During which he can start growing to larger size and hold on to All Might down and crush him from there.

I'd say Chop Chop can win, but he'll have to be quick before All Might starts busting out other tactics to get an upper hand.
 
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