>>44037517Pokemon-wise, I find the two would be pretty evenly matched. From there, it comes down to strategy, mentality and how they handle being under pressure and adapting to surprise changes. Something both have had trouble with, but also can come to expect thanks to Ash. I'd give the dge to Misty winning more times than May would in this regard, but they'd go back and forth on wins for about a 60-40 match up in Misty's favor.
Dawn, however, would consistently thrash them both. Same goes for Iris. Those two are absolutely the strongest and most resourceful of Ash's girls.