Are you using Steam, or games from another service? I've only found 1 or 2 things that didn't work immediately on Steam, but I have an absolute hell of a time getting anything off Steam to run, it's like pulling teeth. Especially older Windows games; they're just a non-starter most of the time.
I just use a single Bottle's bottle to install a bunch of off-Steam games. Contains many older windows dependencies; you have to install them yourself but they are found within the bottle's settings.
I remember trying to get Sims 3 working for my partner, it had all sorts of missing textures, kept crashing and had poor performance. Turns out you need a 4gb patch?? made from the community? Decided to toss it in my bottle and it works flawlessly. Have not tried dos games but may be worth a shot.
From steam, to lutris to base wine to he to trying a couple back cause nothing else worked.
Saw it all, did it all and I hazard a guess I soon will see it all again