If your "server" is really a windows server, and if it's a remotely hosted one, and if you tried to run an IL-2 client game on it to host a mission, then this won't work, because remotely hosted servers usually have no graphics card and no CPU-integrated 3D support whatsoever.
That's one possible cause for this.
If however you really tried to run the dedicated server "il2server.exe" and this one didn't do much or anything, then the most likely reason is DEP ("Data Execution Prevention").
This video tells a bit about what DEP is and how to disable it for certain programs, skip to the 6:25 timemark for disabling DEP on a process:
Because different Windows Server Operating Systems have different ways to access the advanced system properties (the video shows Windows 7 which is not of much help here), let me tell you that typing "SystemPropertiesAdvanced" into the start menu (or the "run" dialog thereof, if you windows OS is ancient) or "sysdm.cpl ,3" and hitting return will do the trick.
il2server.exe unfortunately needs DEP to be disabled, otherwise it simply stops running before it can output anything.
Mike