yet, he has won the Orange League...
but even then, Ash's goal is becoming Pokemon MASTER - who, in the Pokemon world, said that a Pokemon Master is someone who won ONE(!) League? - It is only ever stated that they are the League CHAMPION!
Champion =/= Master
By MY OWN(!!) definition, a Pokemon Master would be someone who would have won several different Regional-Leagues at least once, and has deep knowledge of Pokemon, how to care for them, advanced battle-tactics, and so much more that is to know about Pokemon...
So Ash will NEVER be a MASTER - since he is only focusing on battling. (and the occasional catch to fill up his team)
I mean really... someone who has to ask what Pokemon it is before him, that totally told it's name 10 times in his face... and THEN has to ask the Pokedex about it's name... just cannot be a Master...
A League-Champion, yes... but not a Master.
Gary, despite not having won any League [to our knowledge] is by far, way mor classified to be a MASTER then Ash, even though he has given up on challanging Gyms and Leagues, to become a Pokemon Professor...
In the Original Kanto-Arc Gary had caught, and trained(!) way more Pokemon than Ash in the same amount of time.. Later he still shows more knowledge about Pokemon and advanced battle tactics, than Ash, while traveling alone! (and therefore caring for his Pokemon alone, where Ash always had Brock and his other Companions)
yeah I know Off-Topic, but... eh...