RA2/Yuri's Revenge on Wine on Mac OS X

ra2_yuri_wine

Prerequisites (this is what I use, your mileage may vary):
Mac OS X 10.10.4 running on iMac13,2
XQuartz (http://xquartz.macosforge.org)
PlayOnMac 4.2.8 (https://www.playonmac.com) - N.B. PlayOnLinux available
Wine 1.6.2 (downloaded in PlayOnMac)
The First Decade (TFD) DVD (Red Alert 2 and Yuri's Revenge)
TFD v1.03 revision 4 patch (http://www.cncnz.com/hosted-projects/command-patch/the-first-decade-unofficial-patch/)
  Updates to latest versions of RA2 and Yuri plus NO-CD, TCP (network play) patch and other goodies

Install PlayOnMac
Launch PlayOnMac
Select Tools and then Manage Wine versions
Select 1.6.2 from the left list and install
Insert TFD DVD
Click the + (plus) Install button and select Install a non-listed program
Follow the wizard using Install a program in a new virtual drive, give it a name and accept the defaults
Select CD-ROM : CNCTFD and then proceed with the installer, ignore message about Wine crashing
  Select Custom Installation and untick all games apart from RA2 and Yuri
  Yes to restart Windows at end
  Select Register Later
At the shortcut selection, first select Ra2.exe, give it a name and then Yuri.exe
Select I don't want to make another shortcut to finish
Two new progams should appear in PlayOnMac's window and also on your Desktop
Select either and then click Configure
Select the Display tab
Change the option for Direct Draw Renderer to gdi
Change the option for Render target mode lock to readtex
Close the window
Click the + (plus) Install button and select Install a non-listed program
This time select Edit or update an existing application
Tick the Show virtual drives checkbox and select the drive you created before
Follow the wizard and this time choose Select another file
Browse for the tfd-103-rev4.exe patch and proceed with installation
Eject your TFD DVD
Double click on either game to start
Profit!

Notes:
For Network play you'll need to add a DLL override for wsock32.dll - I have not tested this
  Click Configure in PlayOnMac on either game
  Select the Wine tab and then click Configure Wine
  In the popup dialog select the Libraries tab
  Type in wsock32.dll and then click Add, accept the warning

I have not tested Internet play but looks like it works

I've noticed that RA2 will play fine full screen at 1024x768 but Yuri lags at that resolution - you need to use 800x600
A work around is to use the Wine 1.7.X development version, which I find runs very well - your mileage may vary

Cannis Rules v1.8 mod:
You can play this great mod under Wine too, you just need an extra library so it doesn't crash on open

Launch PlayOnMac
Click the + (plus) Install button and select Install a non-listed program
This time select Edit or update an existing application
Tick the Show virtual drives checkbox and select the drive you created before
Follow the wizard and choose Select another file
Browse for the Cannis Rules v1.8 installer and proceed with installation
At the shortcut selection, select Cannis Rules v.1.8.exe and give it a name
Select I don't want to make another shortcut to finish
Cannis Rules should appear in PlayOnMac's window and also on your Desktop
Select it from the main window and then click Configure
Select the Install components tab
Find and select mfc42 and click Install
Double click on Cannis Rules shortcut to start
Profit!