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So I'm marathoning all the pokemon games, I don't have a Gameboy Colour anymore so I'm playing the old games on an emulator (VBA) on my Mac. I remember back in the day that you could trade pokemon from Gen I to Gen II through the Time Capsule and a Gameboy Link Cable (ahh the days!)

Is there anyway I can do this with the emulator on my mac? I essentially want to bring my Pokemon Red team to Pokemon Crystal. If someone knows of a solution on how to do this it would be greatly appreciated!

If I can't do this on my mac, I do have a windows partition, but obviously a bit more work in doing that.

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Only certain emulators or other third party software can be used to complete this. This video may be able to help:

The user in the video uses a program called TGB Dual which allows you to effectively run two (compatible) versions of the game (i.e. red and blue, or silver and gold, etc.) on the same "console". From here, you can then carry out the trade.

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I've recently struggled with this and you can do it easily using a multiplayer window in mGBA. Open the window, open another ROM from the one in your main window, and they are automatically connected by cable

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    – Wipqozn
    Jul 26 at 14:09
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I'm not sure if vanilla VBA is capable of this, but both VBA-M (maintained fork of VBA) and mGBA (generally preferred by now) emulators do allow it. Specifics may differ a bit depending on emulator: you might have to start two instances of emulator at once and manually link them (VBA-M) or simply use multiplayer setup (mGBA).

As a precaution: it is possible with some tweaking in RetroArch for some cores, but is a pain to get running. Using standalone emulator is highly recommended in this case.

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