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What was the hardest fight for you

Cynthia actually gave me a challenge in DPPt, lost a couple of times to her. Actually, she's the reason why I started to grind more not just in Pokemon, but in video games in general. So beating her in BDSP came pretty easily to me unsurprisingly.

When I was younger I had a little bit of trouble with Morty in Gold, for some reason. Not to the point where I couldn't beat him in the first battle, but I did lose I think one or two Pokemon to him. Funny because every other Johto gym leader was pretty easy, but he was pretty much my first "wall", I guess.
 
Liza and Tate in Emerald (until I figured out Flying types effectively nullified their attacks)
Fantina in both Diamond and BD
Cynthia in BD
Ghetis in Black and White 2
Totem Wishiwashi, Totem Lurantis, and Totem Mimikyu in Gen 7
Raihan in Sword

Those are the ones I remember off the top of my head.
 
I got walled pretty bad by Whitney in SoulSilver as a kid. I remember trying it over and over again, only to get destroyed by Miltank every single time. I think God or some higher power felt bad for me after watching me get obliterated several times, so I finally got lucky in the battle and pulled through. There was also the time I got locked into a battle with Morty due to both our Pokémon being unable to hit each other.

After SoulSilver though, I was old enough to properly strategize and developed enough patience to actually train my Pokémon. I don't recall any particularly tough battles after that point.
 
Drayden's Gym Battle in Pokémon White 2.
My Pokémon were somewhat under-leveled for the fight, and couldn't take attacks from his Haxorus, except my Boldore and Gigalith had Sturdy. However, his Haxorus had Mold Breaker to OHKO the two Rock types anyway. That's when I realized that I had taught my Leavanny Entrainment, which TBF I didn't think would ever help me, but lo and behold, it did. After giving Haxorus Chlorophyll, Gigalith and Boldore could endure his hits and deal damage to him to finally knock him out.

This battle was a turning point for my playstyle as well, for now I started holding deep respect for the seemingly obscure, situational and useless status moves like Entrainment, Gastro Acid and Leer.
 
When I was a kid setting out on my first Pokémon adventures, Glacia and Steven. Served me right to only run a Sceptile with 4 steel-resistsnt moves. Took til it was level 86 for it to beat the Elite Four.


Nowadays as an adult?
Not gonna lie my regular teams got stomped more by Totem Marowak and its Salazzle partners than I ever did by the likes of BDSP Cynthia, Legends Arceus Volo, Ultra Necrozma, BW Ghetsis, Whitney, all those notoriously difficult fights. Something about Teacher Emily in early USUM too...
 
That would be Ultra Necrozma; I still dread battling it with every playthrough. It doesn't help that it's preceded by that damn Ultra Warp Ride, which I have to do several times before I make it to Ultra Meagalopolis. What a drag.

If we're talking strictly trainer battles, that would have to be Morimoto and Cynthia in BW. Both are post-game bosses, and both were confounded by my damn compulsions. I've since modified the compulsions (yes, that can happen, although not often), so Morimoto shouldn't give me too much trouble next time (if there is a next time), but Cynthia, I'm sure, will remain a pain.

My compulsion to not use TMs, but stick with a Pokemon's "native" moves, is less of a hassle in later games because Pokemon the moves naturally learned by Pokemon are far more diverse now. I can't imagine having to play Gen I like this! The challenge might prove to be less "fun" and more "villain backstory."
 
In my solo runs it has been both Ultra Necrozma, which aside from the massive stats it is overleveled, and Kukui, who has Pokémon that hit like a truck and are fast.

After how easy I found Gen VI the opposite happened next gen... Of course, my opinion can change once I start doing solo runs of the Switch games.
 
In the more recent mainline Pokémon games, I think Volo + Giratina was the only battle to ever truly test me. Not that I won it by the skin of my teeth, because I still had two high HP Pokémon at the end of this unprecedented 6v8 battle, but it's definitely the toughest fight any story-mode NPC has given me since Tate and Liza, Juan, and Wallace from all the way back in Emerald.
No, Cynthia in BDSP didn't reach that level of push. I may have been down to two low HP Pokémon at the end of this 4v6 (no I am not joking, and this wasn't even the first time I disrespected her with an incomplete team) battle but I mostly kept total control of said battle and didn't even need a single affection survival for the win. Although the result was statistically closer to defeat, it wasn't as much a struggle as said statistics would suggest.
 
Probably tame for modern day standards, but I'll never forget Lance during my first playthrough of HGSS

I actually didn't beat it for a good couple months or so cuz I was just stuck on Lance lol. I legit thought I would never beat him lol. I'll never forget the satisfaction when I did.

Red also definitely put up a fight, but it didn't feel as stressful as Lance, given I could fight Red fully prepared and stocked with items unlike with Lance given I'd have the team already scuffed up by the E4.
 
My original FRLG champion battle with solo run Blastoise was hard. The Cynthia one in Platinum was also difficult. Also Steven in Emerald. Then Red in HG.

Overall I think the FRLG one frustrated most, it is certainly the memorable one... But the Red one was objectively harder.
 
on regular playthroughs, i have bad memories of rby sabrina and dp cynthia

in terms of nuzlockes, clay was my biggest, saddest, absolute blowout of a wipe of all time (this was on me for not stocking up on healing stuff well enough, but still), so the award goes to him
 
Years ago, I did a nuzlocke in B/W and Clay was the wall I hit and ended up losing too. Clay is pretty tough in general, but man doing a Nuzlocke against him was a nightmare
 

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