Who would win? in Off Topic
Why are we talking about Ichigo now?
The problem with Ichigo typically is he's a plot device by nature, and seems to be written to ass-pull for abilities more than Goku, who's own habit for ass-pulling was bad enough.
I could cite this fine fellow for example as someone with an ability to at the least draw with Ichigo:
But the problem comes is that while Dio Brando can essentially stop time for as long as he pleased (and move within this stopped time-bubble, which is meant to encompass the world as a whole), any fight between the two, if written by Tite Kubo, would provide Ichigo with an ass-pull opportunity to get out of this.
It's one of the many reasons Bleach is so dull, the protagonist is designed never to lose, and would never be permitted by the author to lose. If Ichigo squares up against someone, you basically know what result Tite Kubo has written, even if he takes a 400 episode detour before getting to that conclusion.
This would of course be passable, if Ichigo wasn't so predictably good also. He's never really presented with a proper crisis of conscience, unsure of his overall goal, or ever just loses it and does something genuinely bad with no underlying rationale. The guy has all the personality of a cardboard cut-out of a WWE wrestler, possibly even less, as they do at least change sides once in a blue moon. So he never really does anything cool with this author-designed un-beatable attribution.
Besides, technically Ichigo would have probably died to Nnoitra had not Kenpachi and Nel interfered. He was too worn out in his fight against Grimmjow and Kenpachi pretty much saved his life. Him and Kenpachi also tied in a fight despite the fact Kenpachi considered it a loss. Ichigo loses sometimes, its just never a loss that results in his death.