Check if situation changed after each point.
1) check if you use latest Wine release (that is Wine-1.1.19)
Here is explained how to install Wine-1.1.19
2) set in registry
[HKEY_CURRENT_USER\\Software\\Wine\\Direct3D]
"OffscreenRenderingMode"="fbo"
[HKEY_CURRENT_USER\\Software\\Wine\\Direct3D]
"VideoMemorySize"="YourVideoMemorySize"
You can do this by
this plugin
3) read
entry in AppDB about Half Life 2 on www.winehq.org
4) check if you've got latest stable drivers for your gpu (that is 180.51 version)