My boy had all fully evolved pokemon other than Pikachu of coarse and a Psuedo-Legendary and still lost the finals, at least he finally won and became Alolan Champion but I would be happier if he didn't earn that title when he used Rowlet unironically. Rowlet even KOed itself like Charizard did in the Indigo League in one of his Alolan League battles, by just falling asleep without knowing the move Rest. He even forgets he was the Alolan Champion in Journeys, where he beats Leon to become the world's strongest "known" trainer. To be fair losing to Tobias was just the story writers saying Ash is never becoming Champion, but going up against a team of at least 2 legendaries, possibly a team of 6 of them, was just lazy writing, and Tobias doesn't even become Sinnoh Champion after because he still needed to beat the Elite Four and Cynthia and int BW Cynthia is still canonically Champion. Since we never see Sinnoh's Elite Four members again we can assume either he's now a member or he was..
defeated on the first member, which in the Anime was Lucian. who his Darkrai had a big type advantage against. But his biggest failure to become Champion was BW by far. He lost to Cameron, who wouldn't have gotten 8 gym badges in the first place since he thought the eighth badge was given as a prize for winning the Unova League, a guy who didn't register on time because he thought just getting 8 badges was enough to enter, which AGAIN without Ash's help he wouldn't have been able to compete at all. Then in their battle he even thought a full battle was a 5v5, so he only brought 5 Pokemon to Ash's six, and still won. This means Ash caused his own defeat in the most humiliating way possible since Charizard falling asleep against Richie in the Indigo League. Cameron didn't even win the full League since he lost to freakin Eeveevolutions of all things. We can all agree that Ash's only good League victory was against Crasher Wake, he used amazing strategy, didn't cheat, kept in type...
advantages as much as possible, and even swept Wake's team. The only other time he swept a Gym Battle was against Wattson, where he unintentionally cheated, and even after figuring out he cheated and coming clean Wattson still let him keep the Dynamo Badge. This is not to say the Crasher Wake was the best battle, just the best when evaluating Ash as a trainer.