Mine was Liza and Tate everyone else was pretty easy to counter with my Wingull/Peliper. Mind you Wallce was a slight pain, not too big compared to Liza and Tate though.
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I also found Brawley to be super hard took me like 4 tries to beat him.
brawly and tate & liza are quite tough. i like all the other gym leaders though.
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Brawly is the only one I have problems with. I usually have to sail to the beach and beat the trainers there before I finally beat him
Juan and his Kingdra gave me the most trouble. It just kept using Rest when I was about to KO it, making the battle last for a long time.
Flannery. I always used to lose to her. :/
Brawly. Oh how I hate his Makuhita.. >.>
Stupid Norman. I had a great protect and attack strategy against the Slaking, but his Vigoroth destroyed me.
Tate and Liza. As my two strongest pokemon were Blaziken and Altaria, psychic/rock slide destroyed them. Plus that room is really annoying and took me forever to get to them.
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None are annoying. Unless youre on a nuzlocke and yoir torchic hasnt evolved. Then well... Roxxanne?
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I remember particularly having trouble against Winona.
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Tate and Liza. At least a long time ago. I need to rebeat emerald more recently to say for sure....
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I remember Winona and Tate and Liza completely obliterating my team in Ruby. I almost cried fighting Winona.
The most annoying for me was Wallace on Ruby. My battle against him took forever because that Milotic just wouldn't go down. Winona was also annoying because during my Ruby playthrough, none of my Pokemon were good Altaria counters.
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The alt aria that belongs to winona was the worst thing EVER! It caused me to give up for a year, then restart my save file.
The 7th gym. The dual leaders were hard. It toook my about say twenty times. I just had to focus all my power on one side of the pokemon to win.
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Hands down Winona, starting with Blaziken and with my second being Breloom, it was horrible to say the least, glad there was no Cotton Guard in that generation..
Tate and Liza come a very close second.
With Tate&Liza I completely forgot that Blaziken was weak against psychic types, so I put Blaziken and Gardevoir up bu then the Lunatone got in Psychic and OHKOed my Blaziken. It took me three tries to finally win xD
I don't know why everyone thinks winona is so annoying, she was really easy on Emerald for me.
I really need something to put here.
Winona. I lost to her the first time I battled. Altaria is the reason! I already beat the game already though! XD
The gyms were actually pretty easy especially the duo silence and lunatone due to my swampert and mitotic. The elite four in emerald is what I had problems with
spiritomb with wonderguard........ ugh..,
I always had trouble with Brawly. His gym was annoying to navigate also.
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