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In any of the versions and generations is there a way to rematch the trainers leading up to the gym leader or the gym leader him/herself?

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See http://pokemondb.net/pokebase/46708/in-what-games-can-you-rebattle-gym-leaders

The trainers you are never able to battle again, but the Gym Leaders you are in the games listed above.

Plus, you'll be able to battle at least some of the old Gym Leaders again in the Black and White 2 World Tournament feature. It is suspected that all past Gym Leaders will be able to be battled with this feature, but for now only Brock, Misty, Blaine, Giovanni, Janine, and Volkner are confirmed.

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You can't re-battle the gym trainer but in Heartgold/Soulsilver you can get numbers of gym leaders and battle them on certain days. Also in Ruby/Sapphire/Emerald(not sure about R/S but i know for sure about Emerald that you can) get numbers from gym leaders after you beat them and they will call you for rematches.

Source-Personal Experience

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Forgot about your personal experiences did you? XP
well havent played rub and sapphire for years im doing a nuzlocke on emerald now so yea XD