PokéBase - Pokémon Q&A
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If I want to upload 2 or more Pokemon, is there a way to do it where I don't have to leave the GTS and go back for the second one??

Just go to the GTS Once and upload to or more Pokemon before leaving.

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If u have an R4 card u can load your .sav file of a Pokémon game on PokéGen and then add multiple Pokémon to the .sav file then again put in the r4 overwriting old one this is the only way to put more Pokémon in the game,using GTS method only one Pokémon at a time sorry :(

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Sorry, but it is only possible to download 1 pokemon at a time.

Hope this helps! XD

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