Could May have won the Johto Grand Festival?

She obviously wouldn't have won if Solidad was still there. I could have seen May making it to the finals this time like Dawn did, and putting up a better fight against Solidad, but she still would have lost.

I think its a bit of a shame that just as May was finally becoming a strong trainer and got some fully evolved pokemon.....we stopped seeing her. I always felt May had more potential in her own short spinoff series in Johto (I'd only have it last about 13 episodes, not talking about something huge here, just a short thing), and have it as that. Obviously its too late now though, her character is going the way of Misty.

May was seen to be much more powerful at her Sinnoh comeback (the vs Dawn match doesn't count, since the loss was intentional by the writer's part). She had a Blaziken, a Venusaur, a Wartortle. Imagine if she managed to get Blastoise/Snorlax. She also has Glaceon, which was shown pretty strong when it was still a newly-evolved Pokemon. (again, losing to a plushie for the sake of marketing and DP Contest plot doesn't count). Assuming that she was able to travel by herself around Johto and gathering 5 Ribbons, plus the fact that she always beats one more rival in each GF she enters, I really believe that she beat Solidad at the Johto GF finals, winning the thing.