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R1: Does DIO have The World? If so, I'd probably go with him due to likely having a solid speed advantage, though I don't know if he can actually put Kars down.
R2: Probably Ultimate Kars. DIO has no way whatsoever to put him down, and Kars could probably even just outlast DIO until sunrise, since he no longer has his old weaknesses, and all.
Maybe DIO can use The World as a way to make him generate enough force to send Kars flying into outer space? Seems unlikely but if Kakyoin can be thrown meters across with a single punch, then Kars would be propelled into the air if DIO releases a good ol barrage.
R1 goes to dio, Kars can survive a lot of things but not everything, i would say getting his whole body frozen or laser-eyes is pretty nasty :/
R2 kars is immortal and has incredible hamon powers, even with timestop i dont see how dio could defeat him... maybe inconclusive since i also dont see how kars could harm dio with the world protecting him (unless hamon used on stand = hamon used on stand user, if that is the case than kars easily)...
R1 should goes to DIO if he has The World, since it'll allows him to circuumvent the whole "eat vampire" thing, it's also faster than Kars so it stands a good chance.
If it's without his stand, Dio gets his ass kicked to heaven.
R2 is Kars, it has been shown that hamon powers could affect the stands (DIO refused to directly touch Joseph, even with The World, because he surrounded his body with hamon), he can easily take whoever DIO dish out (and he'll eventually adapt to it) and he can also just wait it out until the sun rise, or he can use his adaptation ability to eventually get an Hamon hit on The World.
R1 to Dio with The World since The World won't get absorbed by Kars, plus it is way faster than Kars so it can kill him via MUDA MUDA MUDA barrages.
R2 goes to Kars as seen that Hamon will affect stands if the user is a vampire, even with time stop Dio have no real way of killing Kars, also with hamon as powerful of what Kars had he would only need to touch Dio to vaporize him, so R2 goes to kars
Regarding round 2, if dio has basic knowledge on Kars then he could potentially stop time, take him and fly into orbit and let him freeze. As for Hamon being too dangerous, he did develop the ability to freeze people in order to combat against hamon so he could use that if he's at his best and accustomed to Jonathan's body.