Whilst the barest of bare anecdata, I can, e.g., run mineways.exe on Catalina 10.15.3 using wine64 4.0.2 (from homebrew) happily[1].
[1] Ok, you have to cancel the "bogus app move to bin?" prompt for both mineways.exe and vcruntime140_1.dll which is messy but I can live with that for OS emulation.
Whilst the barest of bare anecdata, I can, e.g., run mineways.exe on Catalina 10.15.3 using wine64 4.0.2 (from homebrew) happily[1].
[1] Ok, you have to cancel the "bogus app move to bin?" prompt for both mineways.exe and vcruntime140_1.dll which is messy but I can live with that for OS emulation.