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Going with what CP said. Though i do feel that Esdeath could potentially win round 1 ONLY if she manages to freeze all of Dio's body. But since Dio can control his body's temperature(though to what extent, i don't know. But he should have complete control of it), he may possible be able to slow down the freezing process if not possibly even nullify it.
Round 2: Yeah Dio just stomps Esdeath as 1) She can't see Za Warudow, and 2) Even if we do grant her the ability to see and harm The World, it's just too fast for Esdeath to hit not to mention DIO having the ability to spam his TS unlike Esdeath.