In pure speed, Ken surpasses Dio, I think. Ken is fast enough to create after-image against Raoh's eye sight. But of course, Dio's time stop makes the whole speed thing meaningless.
The question is, can Dio get past Ken's Musou Tensei? Sure, Dio can stop time, but stopping time is meaningless to someone intangible. And Dio can't stop time indefinitely (and requires recharge before using again). In Musou Tensei, Ken can attack his opponents, but Ken is intangible against all opponent's attacks (don't ask me the science behind it, since it's anime/manga). And unlike Dio's time stop, Ken can maintain his Musou Tensei as long as he wants. And while Dio can regenerate, but he won't be able to regenerate after being reduced to ashes (which Ken is very good at). And as pointed out by DB, Ken won't be able to harm The World stand, as Ken is not a stand user, but Ken can just ignore The World and go straight for Dio by using his intangibility.
Even without Musou Tensei, I'm not sure if Dio can actually harm someone as durable as Ken. Sure, Dio can freeze people and everything, but would that even work on someone like prime Kenshiro? The man can tank a concentrated force of falling building. Dio's strength is nowhere near that level (he can throw a steamroller, which is something that nameless faceless mooks can do in Hokuto universe), and he has no way to get past Ken's durability.
Dio has more varieties of skills, but I don't think any of those skills would work on Ken. Even if Dio can somehow get past Ken's durability, there's really nothing Dio can do once Ken goes Musou Tensei (and Ken can do plenty to Dio once Ken is in that state). The only way I see Dio winning is if Dio uses The World before Ken can use Musou Tensei and then going for the immediate kill. But given Dio's ego, Dio is unlikely to go for immediate kill (he likes to torture his opponents), which is plenty of time for Ken to use Musou Tensei. And then it's game over for Dio.
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