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I'd say Cure Dream for GoGo due to the shear power difference. Speed is a bit difficult since we don't have a proper speed calc for Dream within her two series yet and we can only start to give her a minimum by using her appaerance in All-Stars (which would make her above Deku). So it is possible that Deku would try to Speed Blitz, though given her durability, he would either tire himself out or she would catch him and then take the win.
For original Yes Cure Dream, a speed blitz by Deku is a lot more possible. If we assume she at least has comparable speed to Deku, then it becomes interesting. Deku is smarter and would be able to plan out attacks, while Dream would still hold the edge in power thanks to her Dream Attack. It could go either way.
I think until we get a solid speed feat from Yes 5, then Izuku wins more times than naught against original Dream and then loses against Dream from GoGo onward.
Oh, speed is equalized now. I'd go for Nozomi than and even if it wasn't, original Yes 5 has a Speed feat now that would put Nozomi on the same level as Deku at 5% (and probably a level higher via scaling).