PokéBase - Pokémon Q&A
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How do I trade between blue and crystal? The ports on the original gameboy and the gameboy color are different.
Also, are there any exploits when trading back to gen 1?

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1 Answer

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If both players are using a Game Boy Advance, Game Boy Advance SP, Game Boy Color, or Game Boy Pocket, you can use a Game Boy Color Link Cable (model number CGB-003), or a Game Boy Pocket Link Cable (model number MGB-008), or a Universal Game Link Cable (model number MGB-010) to connect them. If the cable does not fit, it is the wrong type.

You either need to use a link cable that can connect to one type of GameBoy on one side and a different type on another or use the same type of GameBoy. If I'm not mistaken, the Gen 1 games can be played on the GameBoy Color, and Gen 2 games can be played on the original GameBoy, and both can be played on the GBA.

Source

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3 years in the making
Nah, the original answer was hidden two months ago, as it just explained the method of how you trade from Gen 1 to 2, not how it's possible, which is what I think this question is asking. Still don't know why it stayed unanswered for so long.