Adapted by a
forum post on GOG by user dudalb, here is a short tutorial on how to get the game to run in CrossOver:
1) Install the game normally in CrossOver from the GOG installer
2) Copy the contents of your Tomb Raider 2 install folder to a CD (title the CD "Tomb Raider 2" and burn it. (Be sure to burn it as a cross-platform Mac/Windows disk.) Make sure to leave the CD in the drive. To make sure that CrossOver picks up the CD you burned, enable "Always
Open Windows CDs and DVDs with CrossOver" in CrossOver's preferences window.
3) Download and run the
Tomb Raider Series XP/Vista Multipatch. Without the CD you burned earlier, the updater will ask for a Tomb Raider 2 CD and will not work unless one is provided.
Once the patcher is completed, you can run the game normally - with this patch you don't need the installation of additional C++ runtimes, don't need to run it in a win98 bottle, and the game will stop randomly crashing.