Okay so minus the Orange League, we've witnessed Ash lose league after league after league, most recently losing the Unova league and regressing from the top 4 to the top 8. So which of the 5 major league losses do you think is the most humiliating, depressing, or just down right ridiculous and unfair.
Indigo League in Kanto(Top 16): Lost to Ritchie because Charizard refused to battle for Ash, thus disqualifying him.
Silver Conference in Johto(Top 8): Lost to Harrison due to Charizard falling first after the Dragon Rage/Flamethrower clash with Blazekin
Ever Grande Conference in Hoenn(Top 8): Lost to Tyson after Pikachu fell first to Tyson's Meowth after the Iron Tail clash
Lily of The Valley Conference in Sinnoh(Top 4): Lost to Tobias and his overpowered legendaries after Pikachu and Latios fainted after Volt Tackle/Luster Purge
Vertress Conference in Unova(Top 8): Lost to Cameron after he got a lucky evolution and overpowered Pikachu's Electro-Ball with Aura Sphere to knock him out.