>>40952298Going through each generation;
> KantoKoga - 13 Level Spike + Muk's Minimize spam
> JohtoMorty - Whitney's a pain but beatable with a moderate level team, Morty's Hypnosis + Dream Eater Gengar is a nightmare to face.
> HoennTate & Liza in Emerald - Double Battle with good synergy by the opponent is a monstrous fight
> SinnohMaylene - Lucario without Monferno is a hell of a fight due to the most likely Pokemon players would have to deal with Fighting-Types being Staravia at that stage of the game
> UnovaDrayden - None of the Gym Leaders in Unova are that hard desu, Drayden can be a bit tough due to Haxorus
> KalosN/A - Kalos is either all easy due to exp. share or all moderately difficult due to no exp. share, Olympia's probably the hardest just because of the level jump and the fact Wulfric is a fucking joke
> Alola (Totems)Kommo-o - Aside from maybe Wishiwashi this is the hardest fight due to the predictions the game makes such as the player using a Fairy-Type
Overall I'd say the hardest is probably Tate & Liza in Emerald because most players won't have a team that's that well balanced around double battles (like you might have a Pokemon with Surf or an Earthquake + Flying-Type duo but that's probably it unless you're intentionally planning for that battle), after them I'd say Koga probably mainly because of the pain in the ass system that is Gen I battle mechanics.