Hey y'all, I got this to work pretty easily with the latest version of Wineskin (free, open source software) on OS X El Capitan. Running well on High settings on my 2009 Macbook Pro (old computer, old games).

I didn't see a guide for this using free software (crossover, yuck) anywhere, so I decided to share it with ya.

Here's how I did it, I probably won't be able to help very much if it doesn't work for you. Sorry :(

PS I can't post any links because this is my first post, you're gonna have to google around

1. Download the latest version of Wineskin
2. Install it. (allow running unrecognized software from the internet if you need to)
3. Open it, update wrapper version (I'm running 2.6.2)
4. Hit the + sign, add WS9Wine 1.9.0 (that's what I'm running at least)
5. Hit Create New Blank Wrapper.
6. Name it whatever (I named mine Settlers2_2),
7. Let it download that software for you that it asks to download.
8. Open the folder your new wrapper is in.
9. right click on the new app (Settlers2_2.app) it made and hit "show package contents"
10. Open Wineskin.app in that folder
11. Hit install software, then browse to your downloaded GOG copy.
12. Install the GOG software as you would.
13. (i followed these instructions from the WINE site for settlers 2 10th anniversary edition
a. Download the files d3dx9_29.dll and msvcr71.dll (both 32 bit editions) from a website called dll-files
b. follow the c_drive shortcut in your new app's (Settlers2_2.app) wineskin folder package (that you should already be in)
c. open windows > system32
d. copy the 2 dll files you downloaded earlier to that folder, overwriting any other versions of those files
14. RUN THE GAME from your new .app (Settlers2_2.app) file that you made earlier
15. Run it in windowed mode, it's more stable apparently.

It's been fine for me in 15 minutes of testing. I'll edit this post if it's not after that.

ENJOY mac nerds. Also if you're a linux nerd this should work with whatever linux wine wrapper you want to use.

Hey,

first of all, your how to worked fine and I was suuuuper happy that the game was running after I tried for some time to fix some issues.

But the games crushes after some time running in windowed mode.
I found out that on my mac (mid 2010, Yosemite) I have to set the graphics settings to very low than it doesn't crash that often.
But I still have the problem that sometimes the game crashes out of the blue and if I load a savegame the game freezes. Loading older savegames doesn't fix it, the game freezes again after some seconds.

Maybe somebody had the same problems and knows a fix for it ;)