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Dio probably takes this, Spidey is way more agile but he's gonna have to enter cqc eventualy to ultimately do any rea damage to Dio (thowing things wouldnt do much, Spidey cant throw anything large enough or big enough to kill), and as Dio can regenerate most wounds with zero effort and can flash freeze on contact, Spidey's probably screwed hard. Kinda hard to defeat someone who can heal most wounds and incap and possibly kill you on contact, although if Spidey doesnt get close he likely wont get harmed.
 
He probably could, eventually, if Dio just stood there and let him wail on him as eventually Dio will exhaust stamina healing over and over. But, Dio would probably freeze his arm the first time he tried landing a punch, not withstanding the few thousand that would be needed to beat Dio to a pulp while he doesnt fight back nor heal. So I guess yeah.
 
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