PokéBase - Pokémon Q&A
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As I understand it, you need to beat the main story in order to transfer previous gen Pokemon to black and white. I've beaten black, and put a team together for my next game. So I will use the pearl that the team is currently on, trade it to the current black game, catch said Pokemon again, then transfer to my sister in laws white game.

the question is now that said Pokemon are 'up to speed' in black and white, if I start the game over, will she be able to trade me the previous gen Pokemon I had her hold onto, can I trade them to her before she's beaten the game in the firstplace?

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Yes, but you need to have beaten the First Gym in order to trade. Once you trade, the Pokemon will be allowed, but the Pokemon will not be registered in the Pokedex.

Hope this helps!

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