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Interesting. I think I'm going to vote for DIO because of his Regenerationn, time stop and of course, the Legendary Road Roller Combo. I don't believe MB Megatron has any resistances to time stopping of the sort (though I haven't watched any of the movies so blah.)
This might actually be more of a stomp since none of the Transformers has ever dealt with time stop before (seen just about all of MB's movies, and they never dealt with such hax/ability before).
Megatron doe have the flight advantage and he's of a big...guy(?), that can shoot out blasts that may do quite a number on DIO if not kill him. Though for DIO, he has time stop so he can get out of whatever range Mega's blasts can dish out by time stopping and either getting closer to the latter or get out of range and such. And so long as he's not severely so damaged by the blast if he's caught in it but only on the outer range of it, he'd probably still be able to recover just fine.
But assuming it's not a stomp (can't really truly tell tbh at the same time), i would give it to DIO here after dealing a lot of Muda Muda barrages on Megatron.
Edit: Didn't see the possibly City Block level dura part there of Mega. On second thought, it may be inconclusive on my end but may still go for DIO still just with higher diff.