I do not know if I will be able to help you, but when I want to run a windows game in Ubuntu, I usually follow this steps:
1.- I check if there are some scripts to run this game in Ubuntu. You have ./play.it (
https://www.gog.com/forum/general/linux_playit_weekly_news/post1) and Adamhm's Linux Wine Wrappers (
https://www.gog.com/forum/general/adamhms_linux_wine_wrappers_news_faq_discussion/post1).
2.- If I cannot find this game in both places, I try to use PlayOnLinux. This program is available in Ubuntu it is usually straightforward. I usually check in WineHQ (
https://www.winehq.org/) if the game is compatible with Wine and the solutions.
3.- You can try as well Lutris (
https://lutris.net/). I have never tried it but it looks like very promising
Best regards,
Luis :-)
P.S. I do not use command line, so I cannot hep you with that.( I do not know the reason why you prefer to use command line)