Can Wineskin work with Catalina? I reviewed my previous question, and I think the differences with Catalina merit a separate question.

A double-click or a menu→open on vanilla wineskin or a wineskin-wrapped Windows app has no visible effect (except for showing the icon in the recent items part of the dock).

I verified that the settings in the accepted answer there are still set.
There is an unofficial update of wineskin. It works on Catalina. You can find it here - https://github.com/Gcenx/WineskinServer