There's been two tournaments so far, and soon to be three. In both he was put in a situation where it would be a foregone conclusion. It's safe to assume Ash will lose the third one given who is participating, and that would make three tournament losses. In comparison to D/P, Ash won three tournaments. Why do you think the writers are refraining from allowing Ash to get a tournament win, when he's likely to lose the league as well?