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No online play (appears to be DirectPlay related)

Sadly as of 2015, Freelancer multiplayer does not function because of a bug (lack of implementation, really) around DirectPlay. The Freelancer modding community is still very much alive (FreelancerDiscovery has around 100 players online at any given time) and it's a shame an old game like Freelancer still doesn't work properly with Crossover :(

Try to install DirectX - Legacy. It will set up native dplay.

CrossOver Forums: the place to discuss running Windows applications on Mac and Linux

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