By all accounts, USB support in Windows 95 is pretty poor even with the supplement installed. You probably should upgrade to Windows 98.

Any drivers you can find for DOS will likely be useful for mass storage and nothing else. (Even digital gameport devices like the Sidewinder gamepad won't work with DOS games without some tweaking.)

If you want to do some testing, you can probably find a Linux distribution that will boot from a CD and that has USB joystick support.

I tested a wheel that could be played on game cube/Playstation 2 and pc (by usb), I actually got surprised it worked just fine without any need of drivers 😳 (But, who cares the wheel was a shit anyway)
I cant remember about the other joystick I had (but it should work since it was from the Windows 9x era)

PS: tested on Windows 98

Just go with Windows 98?

I use a Thrustmaster T.16000 and it works great 😀

Well, I upgraded to Windows 98. After installing NUSB, it works great now 😀
Darn. I was hoping I could make this thing work 100% with Windows 95, but I guess it just wasn't meant to be... 😢

I set up a Windows 98SE PC for a guy recently and he wanted to play his old flight simulators with a Saitek USB flight stick (it was pretty nice... can't remember the name though). I couldn't find any drivers, but when I plugged it in it didn't even need any. Windows 98SE just installed it without any fuss (can't remember if it was a generic driver or if it just happened to include the real Saitek driver) and the controller configuration control panel application detected all the buttons and calibration settings as normal.

I think controllers are going to be one of the easier things to get working honestly. Unless they have special features that'd really set them apart, I think most are capable of using generic drivers, similar to mice.