Hardest game battle?

Misty in pokemon red!!!! the starmie was so overwhelming when i first played on gameboy!! I dont know if its changed but that always stuck out in my mind
 
My hardest one was for Cilan of Pokemon Black/White (?) back when i played it on 2010, and playing it Elite Type Leaders on Black/White 2 (?).
 
Bugsy in the Johto remakes is always a problem for me. Even when using Pokemon with a type advantage his Scyther will rip though them. It doesn't help that I am also really under leveled for the fight at that stage in the game.

When I first played Shadows of Almia I could not get past the Two Rampardous for several months until after I beat the main story of Guardian Signs.
 
May 2 when speedrunning Pokémon Emerald.
 
SorveteQuente said:
Lucian from D/P/Pt, surprisingly. Mostly because of his Alakazam with an amazing movepool and his overlevelled Gallade. They gave me a lot of trouble in my battles with him.
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Oooh, yes. I remember him and other players besides myself finding him the hardest of the E4 set by far.

Ghetsis in BW also deserves mention, as does Red in GSC/HGSS due to the level jump. Particularly if you go after him with a monotype team in HGSS without extra grinding beyond beating up all the trainers, haha.
 
red in GSC if you ain't prepared, ghetsis in BW, that damn uhhhh big necrozma thingie in usum, wallace in emerald, CYNTHIA IN ANYTHING. also if your team isn't suited for some of these gyms i swear...chuck in GSC, clay in BW, lenore in BW, brawly in RS (y'all i had to leave and come back later in some playthroughs lmfao), fantina in plat...yeah buddy. lol
 
Everyone in Dark rising series lol !!!!!!
 
Running a Ghost Mono and fighting Lysandre in the Rainbow Rocket postgame was the most recent challenge.

Though, as a nub, I went broke losing to Ghestis too many times. I did wipe out the first run in Pokemon Sun because was underlevelled and I do remember wiping in vs the Sinnoh E4 because I was just underlevelled. The second run for each was fine, but Cynthia brought me down to my last pokemon in Pt. (I generally refuse to use legendaries on my team after realizing how easy they make your game in ORAS. Yes; I did Pt after I completed ORAS).
 
Purity Forest in the original PMD. Every battle in there is hell.

You:
-are reduced to level one.
-all items deleted.
-all money is gone.
-only the leader may enter.
-recruiting Pokemon is not possible.
-99 floors.

Zero Isles, too.

Also a lot of Pokemon Ranger fights are very difficult, but especially Froslass. tbh a lot of Pokemon Ranger bosses are tough, since you can't use moves in these games.
 
The hardest battle i can think of at the moment is probably in HGSS once you've gathered all the badges from Johto and Kanto and you reach the summit of Mt.Silver to challenge Red. The first time i challenged him I was seriously unprepared for the insane level jump. My entire team was still probably around level 50. But if we don't include champions, and maybe just gym leaders, Misty always gave me trouble. Maybe i just have bad luck, but her water pulse from her starmie almost always confused me, plus the fact that it had recover, made it nearly impossible when i was first playing through FR. It doesn't help that my first starter choice was charmander :/
 
Typically speaking I don't think being under leveled is necessarily a given that a fight will be tough as against the likes of Blue in FR/LG and Red in HG/SS you can generally make up for the level deficit by having a well trained team with good type coverage however that goes out of the window when your opponent does the exact same so with that in mind...

I'd say

Cynthia from Diamond Pearl or Platinum is one of the strongest contenders because he covers her Team perfectly and her ability to one shot a lot of Pokemon as a result is unbelievably potent.

Ghetsis from Black and White is also downright Formidable as his levels for that part in the game as well as his team itself can be overwhelmingly powerful. After your fight with N it can be really easy to get overwhelmed by Ghetsis's more awkward Pokemon like Hydreigon and Eelektross.

Evice from Pokemon Colosseum is a nasty match-up because his team cripples any shot you have of being able to set-up on his Pokemon and due to Colosseum generally railroading you into using below average Pokemon he can punish you super quickly thanks to the raw power of beasts like slaking and machamp.

Greevil is also a pain purely for the fact his battle actually intends for you to catch all 3 legendary birds as well as 3 safari zone Pokemon at once. In order to even stand a shot at this you need Shadow Salamance and Shadow Lugia to be walling hits while you pick off his team and even then it's relentlessly difficult.
 
Either Lance gen 1 or Red gen 2 for trainer battles but as for pokemon ultra necrozma hands down the hardest pokemon I've ever faced in all the gens
 
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