Back in the day I used a Thrustmaster Nascar Pro Racing Wheel... the best wheel for the money, and a superb wheel IMHO 😀

Note that there are two versions of that wheel that are (used to be) available... a gameport version, and a USB version.

ThrustMaster makes good stuff. I've got a couple of their Formula T2 racing wheel & pedal sets, and they are generally well-made though the pedal springs are prone to break after many hours of use. You can still find boxed sets on eBay for less than $50. Great for Need for Speed and Papyrus driving sims.

If you've got the dosh (being hand-made out of metal and in relatively limited quantities naturally drives the price up, and this is before we add the shipping cost), look through eBay for any TSW (Thomas Sport Wheel) listings. Most of them were made in the gameport era, if I'm not mistaken, and thus feature gameport interfaces.

They're not too common, though, in which case one of the aforementioned Thrustmaster wheel sets will do the job, likely for a lot less money spent.

I agree your best bet is is an old gameport TM Nascar Pro. It was the best of the mass market wheel/pedal/shifters during the heyday of the gameport era and is still reasonably inexpensive and easy to find on eBay. In good nick it still has a nice feel - personally I love it.

I recently replaced my old "Retro-Rig" set with one and paid about $25 plus shipping. But as others have said it's important to find one that hasn't been over-worked since the springs go soft and the pots loose sensitivity. This can be tricky but I say a clean/bright looking wheel is more likely to be less used, though of course a shrewd seller will take time to buff it up. I passed on several dozen before jumping in.

Unless you like paddle shifting avoid models with no shift lever.

For USB I rely on a trusty Logitech MOMO Force. Not the best by any means but very serviceable and wasn't too pricey. The downside is you can feel the gearing at slow angles of turn if you're paying attention - but during the heat of action it feels fine. The Logi drivers/programmer run under W98 which is a retro bonus. I like Logitech wheels and at some point plan to upgrade to a Logitech G27 with clutch pedal and full shifter.

As NamelessPlayer notes - if money is no object there are a few very enticing hand-made sets out there...

Not sure how/if it would work with Dos games (maybe disable the force feedback 1st) but the original Logitech Formula Force used a gameport. although I've only used the Gameport to USB adaptor that shipped with it.

The build quality was really good, much better then the Formula Force GP and Momo wheel that replaced it.