Ever had a question about Linux but felt too afraid to ask? Well now’s your chance, ask any question about Linux, no matter how noob or repeated it is, and I and others will help answer them.
Previous noob question thread: https://lemmy.ml/post/14261893
How are you launching the exe with WINE? Try doing it via the command line if you aren’t already. That way you may get some more information about why it isn’t working. Its as simple as
wine path/to/your/exe
You could also try something like Bottles, which will let you use possibly newer versions of WINE without modifying your system’s WINE.