Questions
Using a controller with CrossOver and Game Porting Toolkit games on a Mac
Translation layers pass the keyboard and mouse into a Windows game reliably and the controller unreliably. Sometimes the pad appears, sometimes as an unknown device, sometimes not at all, and it changes between versions. The dependable route is to map the controller to keys and the mouse with InputConfig so the game receives input it always understands.
What passes through
CrossOver and Whisky (both Wine) and Apple's Game Porting Toolkit forward HID devices to the Windows side, and a Windows game then needs its own support for that device through XInput or DirectInput. An Xbox controller has the best odds because Windows games expect XInput. A DualSense or Switch Pro Controller often lands as a DirectInput device the game does not recognise. Rumble, the light bar, and gyro do not come through.
The keyboard route
Keys and mouse movement always reach the Windows game, because that is the one thing every translation layer gets right. InputConfig sits on the Mac side, reads the controller, and sends keys and mouse motion. To the game it is a keyboard and mouse. The right stick as mouse look works well for first-person games; the play any game guide has the settings that make it feel right, and the preset library has layouts for hundreds of Windows-only titles written with this route in mind.
Steam through CrossOver
Windows Steam inside CrossOver adds Steam Input to the mix, and it usually cannot see the Mac's controller. Turn Steam Input off for the game and use InputConfig; otherwise you can end up with no input or double input.
Questions
Does CrossOver support game controllers on Mac?
Partly. It forwards controllers to Windows games, but the game then needs to recognise the device, and many do not. Mapping the controller to the keyboard with InputConfig works regardless.
Does Game Porting Toolkit pass controllers through?
Often for Xbox-style pads, less often for others. The keyboard route through InputConfig is reliable either way.