Download & Install
Lifted from Outwars Never Dies (Thanks OWReaper!):
Step 1: Download Base
Biffman over at the collection chamber built an amazing installer from the ground up. It will autoinstall Outwars, Dxwind, and nGlide. It seems to have some issues playing cdaudio so I recommend only running it once and go into the options and make sure "use direct3d" is turned on. After this you'll want to directly run the outwars.exe file.
Step 2: Install Multiplayer Fix
Daniel Collins wrote an amazing program that will fix pretty much all the issues experienced over lan play.
Step 3: Install Gameranger
Signing up for an account is quick and it appears to be the most reliable way to get a match going. Be advised that some people will experience issues connecting if you're locked behind a certain rare type of router. Gameranger itself will give you more details on this.
All these files and more can be found in the master google drive folder here:
In the Misc folder there's even a few development tools and rare finds I've been able to dig up through the years. Be advised the 3rd party tools zip file will throw antivirus warnings due to the presence of a trainer.