Meta Battle Subway PokeBase - Pokemon Q&A
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I know that it is impossible to transfer Gen 2 to Gen 3, but can I transfer my Pokemon in Pokemon Silver to HeartGold?

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If it isn't a Gameboy Advanced cartridge, than there's no way. In Pokemon Diamond/Pearl (Maybe Platinum), you could get them in through the Pal Park and then trade to HG/SS.

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No, you cannot.

Why? Because Generation 2 has no way to connect with Generation 3, and the earliest generation that can connect with Generation 4 is Gen 3, leaving your G/S/C Pokemon trapped there.

Source: Experience

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Short answer:

Nope

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