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Hardest Battle?

Light Arceus

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What's the hardest Pokemon battle you've fought in? What did you find the most complicated about it? What Pokemon were you using? Did you win?
 
Mine was a battle with against red in gold version. it took me a long time to beat him, sence his pokemon was about lv 75-81. i had these pokemon on me atm. Tyflosion L.v 72, Umbreon L.v 64, Ho-oh L.v 60, Starmie L.v 57, Sizors L.v 50 and Crobat L.v 48. i didnt know much about pokemon back in 2000 when i started. his espeon sweep the team, umbreon saves the day when i spammed double team then using faint attack, taking espeon out. his charizard kept missing his attacks, used toxic and spammed protect or moonlight if i got hit by any moves. when i play him now, he's easyer.
 
Mine was a battle with against red in gold version. it took me a long time to beat him, sence his pokemon was about lv 75-81. i had these pokemon on me atm. Tyflosion L.v 72, Umbreon L.v 64, Ho-oh L.v 60, Starmie L.v 57, Sizors L.v 50 and Crobat L.v 48. i didnt know much about pokemon back in 2000 when i started. his espeon sweep the team, umbreon saves the day when i spammed double team then using faint attack, taking espeon out. his charizard kept missing his attacks, used toxic and spammed protect or moonlight if i got hit by any moves. when i play him now, he's easyer.
Mine was also Red.
 
For me, battles where you're trying to catch a legendary Pokemon tend to be the most difficult because you can't just defeat them (as you do in Trainer battles), and you HAVE to make your Pokemon last for however-many turns it takes to actually catch them. My hardest such battle had to be in G2 while trying to catch that Ho-oh. Already used my Master Ball earlier, needed Noctowl for Hypnosis and Scyther for False Swipe (the latter being obviously risky against Ho-oh's typing), plus Ho-oh had Recover . . . .
 
Rematch with Colress in B2. It would've been easier, if my 3DS wasn't blinking red on battery life. Barely beat him in time to save.
 
For Trainer battles, I would say the 3-on-3 nature of Pokemon Stadium and Colosseum's Battle modes inherently made those more difficult, because your opponent still posesses a roster of six but unlike the main series you don't know which Pokemon they'll lead into battle with, so you can't guarantee your lead Pokemon is prepared to counter it.
 
Pokemon Red, first playthrough ever against Lance with a "team" consisting of Charizard and assorted low-levelled HM slaves... Oh the good old days
 
For me, it was probably Ghetsis.

I blew right through N in my White version, but I guess it was just chance, because Ghetsis killed me immediately with his Hydreigon. It took me months to beat him, and I didn't actually figure out how to do it until I got the Black and White guidebook. I still love that Guidebook...
 
For me, it was probably Ghetsis.

I blew right through N in my White version, but I guess it was just chance, because Ghetsis killed me immediately with his Hydreigon. It took me months to beat him, and I didn't actually figure out how to do it until I got the Black and White guidebook. I still love that Guidebook...

It took you months to beat ghestsis? i dont know that is, but i could restart my black to find out.
 
Elesa. Oh dear heavens, Elesa.

I had no good counter to her; my Drilburr might have had a great Nature but his IVs had to be in the toilet as he kept getting nailed by Flame Charge. I was able to get a few hits off of her with my Boldore but Smack Down could only do so much and her Emolga kept using Volt Switch. My Sawk could do nothing against her and my Samurott was totally useless. It took me nearly half an hour to take her down and the entire time I was swearing. That was one of the few times that a Gym leader actually gave me fits; I learned from it and made sure that it didn't happen again.
 
That sounds like me vs. Clair in both Gold and HG. In the latter case, her Kingdra swapped out its Surf for a Hydro Pump, which my Typhlosion was lucky enough to avoid having to face. He also had just enough HP to survive Kingdra's Hyper Beam, and I alternated healing with Swift (Smokescreen? Hah!) for the win. It was still pretty close though, he was my last Mon standing and against a water dragon, too.
 
Red in Gold, Crystal, and Heartgold. Probably because I was pretty underleveled. Espeon or Snorlax would just tear through my entire team in Gold. My teams in Crystal and Heartgold weren't the best, either, so I normally only had one or two Pokes that could even take a couple of hits.
 
Ugh, that champion battle against Steven in Sapphire version. It was just the team I was using, I didn't have anything that was at all good against Steel or Rock types, and looking back, it was a pretty unimpressive team altogether. But it took me months to finally beat him. It was terrible, and to this day I still rather resent him as a character for being so unreasonably difficult.....
 
Roark in Pokémon Pearl. It was my very first Pokémon game and I knew nothing about Pokémon websites that could help me. My team also consisted of Chimchar, Shinx, and Geodude, so that just made it all the more difficult.
 
I would say the first play-through in Pokemon Red's Pokemon League. Of course now it seems easy, but back then it was the first experience of a Pokemon League challenge. Because of this I wasn't prepared with enough support items and my Pokemon were slightly under leveled.
 
I just finished a play through of Diamond, and I didn't realize how high-leveled the Elite 4 were until I got there. I was able to beat them after 3 tries, but they put a good fight.

Not the exactly the hardest, but certainly the hardest one I've had in a while.
 
Cynthia in Pokemon Platinum was among the most difficult of in-game trainers I can recall. I conceded defeat 2 or 3 times against her. I even had to resort to prediction tactics and even attempt to employ a strategy. I did however, handicap myself with the inability to use Full Restores and Revives. My team consisted of Torterra, Staraptor, Luxray, Vaporeon, Houndoom, and Giratina. Their levels were 57-61. The natures were for the mostly beneficial and they had a good dose of Effort Values in through vitamins. (Giratina had an Adamant nature, 31 IVs in Attack, and at least 100 EVs in Attack for example.)
 
Wallace in Emerald version. My Emerald team was not the best, and my only thing strong against water types was my Breloom (I also had a Swampert, Sharpedo, Torkoal, Swellow, and Aggron). I managed to finally take down Milotic after constantly needing to revive my Breloom, but I still had to take down his Gyrados. His Gyrados was able to take out my Breloom in 1 Hyper Beam, and all I had left was my Aggron. Luckily, I had just taught my Aggron Shock Wave before the league, and she was able to take down the Gyrados in 1 hit while it was recharging from that Hyper Beam. I have never had a battle come that close before.
 
Cynthia in Pokémon Diamond was one of the hardest battles I faced. Even though I had level-grinded my Pokémon team, which was composed of Empoleon, Luxray, Floatzel, Noctowl, Carnivine and Weavile, into the low 60s, the Elite Four still put up a good fight, which caused me to have a hard time against the Champion herself. I defeated her after a couple of tries, but I will never forget the satisfaction I had when I finally did. Surprisingly, I did not have as hard of a time in Platinum. Even though I had almost the same team, only switching Carnivine for Roserade, I was well-prepared then, which helped a lot.
 
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