https://bugs.winehq.org/show_bug.cgi?id=40276
--- Comment #4 from winetest@luukku.com --- (In reply to Xylemon from comment #3)
It may be worth trying out the latest Staging version of Wine again (don't launch it in fullscreen mode in a virtual window however, it will crash)
Correction, launching Half-Life in fullscreen regardless of a virtual window will cause it to crash in Staging.
I think Sebastian already fixed this. See bug 42262.