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So Shadow Man has a slight AP advantage (614 vs 666 zettatons) and they should be comparably skilled.

That being said, Espio's ability to turn invisible and camoflauge should give him an advantage in being able to avoid projectiles and use sneak attacks on Shadow Man, so Espio gets my vote.
 
Doesnt Espio like....stomp this? I mean, just look at each other abilities, and Shadow Man doesnt have any hax or something like that to close the huge versatility gap
 
It's important to note that Shadow Man single handedly defeated Neptune in Megamix, who likely has thousands of years of experience.
 
Espio can also become intangible, and assuming he's as skilled as Sonic he'd scale to his feat of defeating Emerl
 
True. Also, this version of Shadow Man seems to use teleportation for combat in character. Thought that was worth noting.
 
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