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Win via KO, incapacitation, or death. SPEED EQUALIZED (yes, unfortunately to make this fair I have to throw out the one common factor between these two)
I'd say Ruby takes this. She's shown better fighting capabilities than classic sonic, and her flight and special intangibility gives her superior mobility. Only way I can see Sonic winning this is if he uncharacteristically smart with utilizing his shields, which, might I add, only work against 2 of the 4 types of dust Ruby uses. Ruby's also smart to know when to resort to long range combat as oppose to close range, so Sonic's AP shouldn't be much of a problem. (Even though he's not even twice as strong.)
Ruby FRA. Because she once won a fan-made One Minute Melee between the two and everyone lost their shit. And to keep up Sonic's reputation as a punching bag.