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My friend has an original copy of the game and was wondering if he could play online with me if I buy the HD version on Steam.

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The HD version of Age of Empires has had its networking code rewritten to use the Steam matchmaking service. It is incompatible with the original as far as I know. – jw013 Apr 5 '13 at 0:57
@jw013 That does work as an answer... – Yuuki Apr 5 '13 at 0:58

According to the developers, the game's multiplayer mode will not be compatible with the original:

I have the original Age of Empires 2. Can I play multiplayer matches with my friends who have the new HD version?

Age of Empires 2: HD Edition uses a different multiplayer service than the original version, so cross-platform matchmaking is not possible. You will need to have the same version as your friend in order to play together.

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