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After thinking on this I'm leaning more towards bolas, mostly due to knowledge. And if all else fails he can go to another plane, make a plan and go back and probably win that way. Though I doubt either could fully kill the other so . . . . High difficulty bolas worst case scenario inconclusive...
Honestly would say Kira both rounds.
For round one dio never gets serious unless he realizes the opponent is a threat. like he did with jotaro and his gang, he only killed them when he realized they were threat. And even then knowing how killer queens bomb doesn't mean he's not going to rely...
In character probably Kira. Dio would spend too much time gloating that he's won, without figuring out what killer queen can do and it will cost him the match