Been trying to get this game streamable for days now with mixed results
In OBS Studio I've tried both game capture and display capture with all the config settings (directdraw, direct3D, 3Dfx glide) with no luck.

I've tried dxwnd to window the game but cant get it to start in a window.
Also tried D3Dwindower which does work in making the game windowed, however it stretches the screen to desktop resolution. This can be somewhat fixed by putting the desktop res to 800x600 (the resolution I want to run the game in) but then the screen is slightly squished as the header bar of the window takes up a chunk of space.

Of course I could just set my desktop resolution to 1024x768, but would prefer to have the game full screen windowed if possible.

So I guess dxwnd would be the best option to make the game fullscreen windowed in order to stream it, but I cant figure out what settings I need to make it windowed using dxwnd.

Any help would be much appreciated.

… I thought this game supported windowed mode natively?

The native windowed mode disables mouselook.

Mouselook works in windowed mode if you use the dgVoodoo wrapper and run the game with the Direct3D renderer. Run dgVoodooCpl.exe and change the setting on the first tab from Fullscreen to Windowed.

This doesnt seem to work. I set the game to Direct3D mode and used the dgvoodoo wrapper with the windowed option and its still fullscreen.

Do you see the "dgVoodoo" watermark in the lower right corner when that option is enabled in dgVoodooCpl.exe? If not, then you might not have copied the right files. You should have DDraw.dll and D3DImm.dll (both from the "MS" folder in the dgVoodoo archive), and I suggest also copying dgVoodooCpl.exe, running that copy in the game folder and clicking on the [.] button near the top so that your settings are saved in the current folder.

You need to go to DirectX tab in dgVoodooCpl.exe and set "Application controlled fullscreen/windowed state" to off.

Very sorry for the late response guys, but thanks, I got the dgvoodoo watermark showing now.

Unfortunately now its doing the same problem as when I use D3D windower, where the screen is automatically stretching to fit my widescreen desktop resolution, no matter what scaling settings I choose in the options.

Any ideas how to keep aspect?

Are you talking about in fullscreen? If so, it may be your monitor doing the stretching. Play with the buttons on your monitor and see if you can turn stretching off. If that's not it, it could be your graphics software. Check in your AMD, Nvidia or whatever control panel for an aspect ratio control.