Some years ago I bought it on GOG and run it with Linux wine. Now, I try to play it again but it doesn't work anymore with the latest Ubuntu 14.04 LTS 64 Bit and Wine 1.9.

Is there a chance, you distribute it with a nice wine wrapper for current distributions?

Downloaded the latest 1.1 version and ... it didn't run with the latest wine. But only "Outcast 1.1.exe" doesn't run. Starting "OC1.1.exe", it works as expected! :-)
"Outcast 1.1.exe" seems to be the starter with configuration options. You can do the configuration in userdata/config.ini