What is Ash's worst League lost?

[Xenon Blue]

How Ash vs Cameron should have played out with the same lineup:
Stoutland vs Oshawott -> Oshawott (recall)
Swanna vs Unfezant -> Unfezant
Samurott vs Unfezant -> Samurott
Samurott vs Pikachu -> Pikachu (recall)
Ferrothorn vs Boldore -> Ferrothorn
Ferrothorn vs Pignite -> Pignite
Hydriegon vs Pignite -> Hydriegon
Hydriegon vs Oshawott -> Hydriegon
Hydriegon vs Snivy-> Snivy
Riolu/Lucario vs Snivy -> Lucario
Lucario vs Pikachu -> Lucario

tbh still looks like a bad battle, but at least it's passable and Hydriegon is actually saved as a "secret weapon" rather than just leading off with it.

 

[CMButch]

Torn between Kalos and Unova league. Kalos because he should've won and Unova because he lost in a worst possible way.

 

[Navin]

How Ash vs Cameron should have played out with the same lineup:
Stoutland vs Oshawott -> Oshawott (recall)
Swanna vs Unfezant -> Unfezant
Samurott vs Unfezant -> Samurott
Samurott vs Pikachu -> Pikachu (recall)
Ferrothorn vs Boldore -> Ferrothorn
Ferrothorn vs Pignite -> Pignite
Hydriegon vs Pignite -> Hydriegon
Hydriegon vs Oshawott -> Hydriegon
Hydriegon vs Snivy-> Snivy
Riolu/Lucario vs Snivy -> Lucario
Lucario vs Pikachu -> Lucario

tbh still looks like a bad battle, but at least it's passable and Hydriegon is actually saved as a "secret weapon" rather than just leading off with it.

It's still bad because if Ash bothered to use Krookodile, Leavanny, and Palpitoad instead of Oshawott, Snivy, and Boldore, he'd have won.

Give credit to Johto Ash at the Silver Conference. He knew he wasn't going to beat Gary or Harrison without abusing Charizard and Snorlax, and he did just that.

 

[AuraChannelerChris]

The Unova and Kalos leagues were equally bad. You really can't talk about the losses without bringing up how badly structured they were that led to those moments.

Unova because of the total ******** that was the brainless trainer who got way too many Deus Ex Machina moments against Ash and won (how the hell did that Riolu manage to stay like that without evolving this late, for example), and the damned filler league episodes that could have been used to develop the trainers. Ash's fried brain when he brought babies to fight against monsters. Virgil was such an annoying tease but I would have liked Ash losing to a plethora of Eevees since that would've been like a Type test. I'd say Decolore Islands just existing prevented Ash from properly developing his team for this league.

Kalos because it was overhyped to hell and back with the sacred legendary Greninja of legend, and the insanity that was Alain's heavily plot-armored Charizard. There is also the fact we only fully got to see Ash fighting in two matches (Unova has no excuse with that stupid closure to Trip's rivalry with Ash). The director wanted to balance things out by showing Scottie Shota Sawyer and Alain decimating people and taking names, but Sawyer was sooo forced to be acknowledged as this impossible opponent Ash wouldn't beat, and Alain...well, the mere fact he was convinced to enter at 0 badges within the span of a week to get them all in record time was the epitome of ridiculousness.

Long story short, Unova was bad because of generic stupidity, and Kalos was bad because of randomness. Both, though, had absurdity behind their premises.