Can we all just appreciate the fact that... If DIO had dropped the Road Roller just a single second earlier, he would have won then and there? Waiting so long was a huge tactical blunder on his part, and allowed Jotaro to get the upper hand, which was only made worse by DIO making mistake after mistake in dealing with Jotaro after-- or even before his legs healed.
If he had kept The World close to him, for instance, as opposed to sending it some distance out, perhaps its leg wouldn't have been as badly obliterated by Star Platinum's close-to-Jotaro-range punch.