I am a Mac user running Voobly on Wine (not Wineskin, Winebottler, etc) and have no problems starting up the app. In the same Wine instance I also have the GOG version of Star Wars Galactic Battlegrounds that now runs (nearly) flawlessly on its own as well. However, in order to make multiplayer work I needed to make sure DirectPlay was installed, which I did using Winetricks (sh winetricks directplay).

When I join the SWGB room, however, I get this error:
"Non-DirectPlay game path is 'C:\Program Files\Star Wars - Galactic Battlegrounds\Game'
Verifying 'C:\Program Files\Star Wars - Galactic Battlegrounds\Game\language_x1.dll' exists...
Success!
Voobly path is 'c:\program files\voobly'
Game version is '1.1'
Checking DirectPlay libraries...
Looking for dpwsockx.dll...
Failure!

DirectPlay failed to load properly. This is probably an OS installation bug. You might need to reinstall your operating system. Windows 8.1 and later users can install DirectPlay through Control Panel -> Programs -> Turns Windows features on or off -> Legacy Components -> DirectPlay."

I don't have access to the Control Panel using Wine, but I did check the system32 folder and dpwsockx.dll definitely exists. Has anyone encountered anything similar and know how to get SWGB to run with Voobly on Wine?

I was able to resolve the issue with the DirectPlay dlls in Wine, but encountered another issue. When I try to launch the game, I get the following error:
<Game was not rated - reason: game was not finished>

This appears to be a known issue ( bug ID 29384 on Wine's bugzilla) with Wine, however there haven't been any updates in a while in that bug log. Additionally, the only game mentioned there is AOEII. I have seen reports here and on other sites of users successfully playing SWGB multiplayer. Does anyone know how to get around this bug? Are you using Voobly or something else?

According to the comments in that bug you need to apply the staging patches and launch wine with STAGING_WRITECOPY=1.

From my limited understanding of what was discussed in the text of that bug, I thought wine-compholio was a separate test version of Wine. I'm not even sure that patch would work if I applied it to the real deal, nor am I sure how to do that last step.

You should read through that page. Installation instructions if you aren't compiling it yourself. The last step is setting an environmental variable before starting Wine:

Apologies if I'm being thick or missing something on the site, but I already have Wine Staging installed (it came in the initial WineHQ packages I downloaded and it's the default app that my .exes are opening in) and it still isn't clear how I am supposed to apply additional patches. Sources of my confusion:
1. The website you linked makes it seem like all available patches are already applied in Staging. If so, shouldn't Voobly work for me? (Yes I tried entering the export command mentioned in the last post and then opening the Voobly exe)
2. The .patch link in the Bugzilla thread opens up a webpage with embedded text, but I don't see any kind of file I can download.
3. Neither link above explains how to apply a specific individual patch. Is there a command I can run for this, and if so, how am I supposed to reference the patch? Is there supposed to be a file, or just that link?

First time you mentioned that you installed a Wine Staging build. If you are starting from a terminal be sure you are launching Wine Staging and follow these instructions. You don't. Those are source code patches which need to be applied to the source. Which means one would need to build from source to use them. Sidenote: Homebrew is pretty damn slick as long as you are using something newer than 10.6. However, you don't need to as the patches mentioned are already applied to the Staging build that you have. I would expect it to barring regressions. Then again I'm not sure how well that patchset is tested on OS X. Location of the prefix and possibly SIP could factor in?

I managed to get this working with a little tinkering. Thanks for the help.

Cheers.