>>33382938He actually tends to win at competitions or goals that are unrelated to winning a Pokemon League. Like the one time he won the Orange League or the Battle Frontier. He even succeeded at arguably his most notable goal in DP which was to defeat Paul.
Honestly most series feature Ash having some sort of major victory or goal achieved.
>OS He lost the Indigo League which gave him a massive wake up call then won the Orange League and defeated Gary at the Silver Conference>AG He lost his major goal of winning the league but his new major goal of completing the Battle Frontier he managed to achieve>DP He lost the league but defeated Paul which was his major goal in Sinnoh. He also was the only person in all of Sinnoh to defeat not only Darkrai but also the only person to ever see, let alone defeat Tobias' Latios>BW I didn't watch>XY He lost the league but gut the furthest ever before and mastered a new type of evolution with his Greninja and also saved the entire world which I admit means jackshit to him but hey it's somethingChances are that Ash will graduate from the school but then lose the league or the battle with Masked Royal after completing all trials.