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  #26    
Old February 9th, 2013 (5:02 PM).
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    Trying to fight Claire in SS with only Pokemon based on predatory animals. Also they're underleveled.
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      #27    
    Old February 9th, 2013 (10:48 PM).
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      Definitely Whitney. Her Miltank has godlike strength.
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        #28    
      Old February 10th, 2013 (7:51 AM).
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      DowntownDumpling DowntownDumpling is offline
         
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        I found the battle with Cynthia in Black to be very difficult.
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          #29    
        Old February 10th, 2013 (10:35 AM).
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        RenegadeClyde RenegadeClyde is offline
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          Morty and Whitney in GSC: The only problem I had with Morty was his Gengar. DAT HYPNOSIS. In my first battle with Whitney, I lost badly. (Miltank's rollout totally slain my Quilava. ) But for some reason I've won the second battle easily. (Maybe because she kept missing the rollout. '-')
          Steven In Ruby: It was a tough battle, especially when I was fighting against his Cradily and Armaldo.
          Iris in White: I did not have ANY Pokémon that could fight against dragons. And her Haxorus is insane.
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            #30    
          Old February 14th, 2013 (12:15 AM).
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          Shayminlover123 Shayminlover123 is offline
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            Either Glacia in Emerald or Aaron from D/P/Pt
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              #31    
            Old February 14th, 2013 (6:44 AM).
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              Candice with that arsewipe Frosslass in Snowpoint, underlevelled squad and type mismatched.
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                #32    
              Old February 14th, 2013 (7:17 AM).
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                I'd say Wallace in R/S as a gym leader and as the champion in Emerald. Didn't he have a Kingdra that was a enormous pain?
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                  #33    
                Old February 14th, 2013 (8:46 AM).
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                  Honestly never saw what the fuss about Whitney's Miltank was; I mean they gave you Machop in the exact same city. It had super-effective against the entire gym and in addition resisted Rollout.

                  On-topic, probably Red in the original Gold. I did a Jigglypuff solo run a while back and I had to grind it to 100 to get there (and even then I had to use half a dozen revives/full restores).
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                    #34    
                  Old February 14th, 2013 (12:06 PM).
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                    My hardest battle was Volkner in Platinum. My highest lv was a lv 56 Empoleon. All my others were below lv 40.
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                      #35    
                    Old February 21st, 2013 (9:03 AM).
                    Toutebelle Toutebelle is offline
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                      Iris in Black 2. She was a nightmare. This was during the rematch - she wasn't too bad for the initial match. Her first four Pokemon didn't put up a fight, but her Archeops was a killer with its Stone Edge and Acrobatics. Then, when I finally beat it, she pulled out the big gun: Haxorus. That Haxorus was the hardest Pokemon I ever faced, what with Dragon Dance and Outrage. It took me 15 Revival Herbs. Luckily my Chandelure's Flame Body was able to burn it. I kept spamming Revival Herbs until the burn caused Haxorus to faint. Thank God Iris used up her Full Restores before Haxorus. (At least this was normal mode - if it were Challenge Mode, Iris might have used a Full Restore.)

                      Nishino in Castelia City was also hard. His Lickilicky had four uber moves and they kept fainting my Pokemon.

                      Cheren was pretty hard for a first Gym Leader. Riolu had no good Fighting moves, and Cheren's Lillipup kept using Work Up.
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                        #36    
                      Old February 22nd, 2013 (2:49 AM).
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                        My hardest battle by far was way way way back in the day when i had just gotten my first ever copy of red. I had never played pokemon. Not even knowing what to expect from the elite four, i rushex in and Agatha that old hag beat me so many times. Her gengar rocked me. Ughh, i hate you Agatha.
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                          #37    
                        Old February 22nd, 2013 (3:23 AM).
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                        Elaitenstile Elaitenstile is offline
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                          Cynthia in Black. Definitely the best, that Garchomp + Outrage and Eelektross + Dragon Claw wiped me off. First my Hax, then Excadrill, and creamed everyone else as well. Next time I took in Reshiram and Kyurem... I feel sorry now.
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                            #38    
                          Old February 28th, 2013 (3:10 PM).
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                          Allons-y
                             
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                            For me the hardest battle I've ever had is Shauntal in BW1, she managed to DESTROY my Arceus in lvl 89, even with type disadvantage.
                            Second, I think is Elesa in BW2, I hate that Emolga.

                            Besides that, Cynthia in BW2 is a *****.
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                              #39    
                            Old March 2nd, 2013 (11:31 AM).
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                            Relith Relith is offline
                               
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                              Surprisingly, I had a good time with Red. (I used the exact same team he used, but I had lower leveled pokes)

                              Whitney's miltank kept rolling my pokemon for 3-6 days before I finally prevailed.
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                                #40    
                              Old March 3rd, 2013 (7:15 AM).
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                              怖がらないで
                                 
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                                Mine was May in Emerald, in that Cycling Road route. Our Pokemon had the same levels, but her Combusken was very hard to defeat. ): Second has to be Whitney and her Miltank, and Brawly would be the third, I guess.
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                                  #41    
                                Old March 4th, 2013 (8:17 AM).
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                                • Silver Tier
                                 
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                                Red on the Gen II remakes was pretty darn hard. I had to trade over some of my better Pokemon from Diamond version to battle him. Took me two tries and a crazy amount of Pokemon reviving and health restoring.
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                                  #42    
                                Old March 4th, 2013 (9:00 AM).
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                                Nyeh?
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                                Wallace in Emerald. I hated going against that Milotic. Red in HG/SS comes close.
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                                  #43    
                                Old March 4th, 2013 (10:31 AM).
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                                skyluigi2 skyluigi2 is offline
                                L-let's a-go...!
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                                Honestly, Sidney from the Hoenn Elite Four. I HATED him so much. That Shiftry... and Cacturne, not to mention I always picked Swampert. I got beaten by that guy so many times.
                                The rest of the Elite Four in Hoenn? Champion? Pushovers. But Sidney... *shudder*
                                Second has to be May when she's in front of the Lilycove Department store. I wanted to get in there so badly, but no matter what I did, my Pokemon always seemed drastically underlevelled for that battle. Took me so long to beat.
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                                  #44    
                                Old March 4th, 2013 (1:19 PM).
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                                Babebraham Babebraham is offline
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                                Rival as the champ in Red. I had an oddish left and he had a venasaur left and it took me an hour to beat him by using cut.
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                                  #45    
                                Old March 4th, 2013 (3:00 PM).
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                                Mr. Whiscash Mr. Whiscash is offline
                                Unegged Hatch
                                   
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                                  Oh god I suddenly started having Flashbacks to Cynthia in Diamond version. I repeat, oh god.
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                                    #46    
                                  Old March 4th, 2013 (3:32 PM).
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                                  Mr Cat Dog Mr Cat Dog is offline
                                  Frasier says it best
                                     
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                                    The hardest battle that I eventually won was Ghetsis in Black. It took me three attempts to do so, and it ended up in a 1-on-1 battle between us. It's also one of the few battles that I've physically felt exhausted after finishing it, which never normally happens with me in Pokemon games. Granted, I was probably a fair bit underlevelled (which also never usually happens) but still... it was hard, guys!
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                                      #47    
                                    Old March 4th, 2013 (6:38 PM).
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                                    B-L-A-Z-E B-L-A-Z-E is offline
                                    リズ
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                                    My opinion on this has changed over the years, and currently I have to say Sabrina from yellow or Whitney from gold and silver if I start with Chikorita.
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                                      #48    
                                    Old March 4th, 2013 (8:32 PM).
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                                    Altair Altair is offline
                                    Willpower
                                       
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                                      Pokemon Champion Gary/Blue in Pokemon Yellow, I can barely remember the fight as I was much younger, however that Arcanine proved to be a handful.
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                                        #49    
                                      Old March 5th, 2013 (2:36 PM).
                                      X-Lan X-Lan is offline
                                         
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                                        I agree about may under the cycling road, the starter in that battle was always vicious.
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                                          #50    
                                        Old March 5th, 2013 (4:04 PM).
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                                        Munchlax11 Munchlax11 is offline
                                        Munch?
                                           
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                                          I remember battling my rival in firered when he was champion. On like my 15th try I beat him on a lucky critical hit after my Blastoise luckily held on at 3 HP.
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