I searched this whole forum for some help in getting the GOG version of Unreal Gold to work on Mac OS X but I didn't see anything helpful so maybe the following can help anyone trying to run this game. I have most of the bugs worked out, although not all.

First up, this is a Windows-only game and you will need Wine. There are basically two choices for a Wine front-end: Wineskin or Crossover. Wineskin is free and Crossover costs money. I have gotten better results with Crossover (trial version) but I am going to give the steps for Wineskin here.

1) with Wineskin, running the app opens something called Wineskin Winery. From here, you can hit the + icon to install the newest Wine engine. As of the time of this writing that is WS9Wine1.6-rc1X. Then, you click "Create New Blank Wrapper" to start the process of creating a Mac OS X wrapper around a Windows app.

2) Give the wrapper a name (Unreal Gold.app). Click OK and wait kind of a ridiculously long time for it to finish. You might get a prompt from the firewall to allow incoming connections -- it doesn't seem to hurt to deny this. When it finishes, go ahead and say "View in Finder". If you clicked to dismiss on accident, you can find the file in /Users/yourname/Applications/Wineskin.

3) Double-Click on the application wrapper you created in the last step. This starts the Wineskin menu. Click "Install Software" then "Choose Setup Executable" and give it the GOG installer exe you downloaded for Unreal Gold. Click "Options" and de-select the "Install Adobe Reader" and the "Create desktop icons" because these are meaningless steps if you're not really on Windows. When the install has finished, select the executable that will be run by this Wineskin: Unreal.exe.

4) Before you're done, I've found that a really important step to avoiding graphical problems, is to click "Screen Options" in Wineskin, and then change the following settings:
* Override
* Extra Gamma Correction: move it about 70% of the way to the right.
* Check the box for "Use Mac Driver instead of X11"
* Uncheck the box for "Decorate Windows"
* Under override settings select "Fullscreen"
* Resolution: Current Resolution
* Installer Options: Force normal windows
* Click Done.

If you ever need to go back to the Wineskin configuration settings, right click on your "Unreal Gold.app" and select "Show Package Contents" and you will see Wineskin.app there. Run that. Every "Wineskin" works this way, and is configured individually.

One more tip:
* When you run Unreal for the first time you might think Direct3D won't work and that you want OpenGL because Mac OS X doesn't have Direct3D drivers. Well Direct3D actually works fine thanks to Wine, so select that.

I had hoped I would be able to install the fan-made 227i patch but this seems to break my install under Wineskin. It successfully installs under Crossover, though. This patch adds OpenGL and a ton of other configuration options, but it breaks the Return to Na Pali campaign. Yes, I triple-checked that I was getting the version of the patch made for people with GOG Unreal Gold. It is either a bug by the patch developer or it is an effect of running this stuff under Wine. Either way, you might want to stick with the base GOG version if you're interested in playing the RTNP campaign.

While I haven't personally played rtnp on 227i (I think i was using 227h at the time) there should be no problems running it so I'm fairly sure it must be a wineskin problem there.

Its probably worthwhile checking on oldunreal.com to see if anyone else has encountered the same problem. The sad thing is that the same person who develops the 227 patches actually natively compiled Unreal for MacOS X but epic won't let him release it because "not enough bandwidth" apparnetly but then epic games doesn't make pc games any more they just make engines so I guess we shouldn't be surprised.

I've read about his unreleased Mac OS X binary, I wish he was able to share it too. If I get the RTNP campaign to work with his 227i patch applied then I will come back here and share details again.

The funny thing is, the Wikipedia page claims that Unreal had a native Mac OS release a year after its release on Windows. But then I remembered, it would have been a PowerPC binary. Doh!

Heya, just followed the tutorial on Wineskin you posted. I don't know if it's specific to my Macbook's video card, but replicating the steps shown here results in the top half of my display being covered in garbled graphics if I attempt to run the game in fullscreen. This occurs regardless of resolution (native or default 640x480). I'm using the absolute latest stable Wine binary (1.7.0).
The only way I've found to alleviate this problem is by running in windowed mode instead.

EDITED FOR CLARITY:

I've found some fairly simple and effective workarounds for those who are experiencing similar difficulties to me in launching the game with stable display.

1) Download OldUnreal's enhanced OpenGL drivers, and use them instead of the old, buggy and generally crappy stock Direct3D7 driver. This will eliminate the screen garbling which can obscure the game view and generally look nasty.

2) The game may still experience bugs when attempting to switch resolution. Switching from the in-game menu may result in an incorrect and cut-off display, and then switch back to the default 640x480 resolution after a few seconds. To get around this, escape out of the menu altogether so you are in-game. Then, bring up your console by pressing the tab key, and then type 'setres', followed by your desired resolution (for example, I used "setres 1280x800", then hit return. The screen will still be cutoff and garbled, but to get around that, all you have to do is restart the game by again pressing tab, typing 'exit' and then hitting return. Relaunch the game, and voila! You can now run Unreal in your preferred resolution!

Usually when one is having garbled graphics it can help to run Winetricks ddr=gdi (right-click wrapper -> Show Package Contents -> Wineskin.app -> Advanced -> Tools -> Winetricks). (I know this htread is old, but it might help people in the future who come across it)

Hello all!

I just wanted to update everyone with good new of Unreal Gold on OSX!

First get Wineskin! Get the newest binaries. Create a new skin and install the GOG version of Unreal Gold!
next get the latest update from Old Unreal:
www.oldunreal.com/oldunrealpatches.html
Install them the same way you did the game. Click the install button in the wineskin app. find the Unreal patch 227i binary and run it!

www.oldunreal.com Join the forums! The updated game has awesome multiplayer servers too.
BTW I've updated my graphics with the hires updates for Unreal Gold!
www.unrealtexture.com

UNREAL GOLD ON MAC/WINESKIN / doesnt work anymore...

Hi!
Lately, when I am running Unreal Gold via Wineskin Wrapper on my Mac 2,4 Intel Pro, it installs "Game Spy" instead of my Unreal Game... Aaah! Why? How to access my game data?
Any hint is highly appreciated :)

Thanks.
Game on.

In your Terminal, type:
open ~/.wine

Then, go into the C drive and look for GOG Games/Unreal Gold
From there, you should find what you're looking for.

This worked for me on an iMac (refurbished 2009 model) running Yosemite.