I've had some issues loading a game I downloaded, and I'm not sure what the issues are. I'm currently using macOS Catalina version 10.15.3, and I've been running wine from the terminal as I have to type wine64 to load the game. I'm pretty sure the game has all the files it needs - from a quick glance I'm assuming some of the files (eg. the saves/profiles) that weren't found should have been created after launch.