Wine will let you play Microsoft games, but older games often require an older version of Wine. Wine keeps changing with changes often causing incompatibility between parts of the programme. What Wine developers call "regressions." If your games are more than two or three years old, they may not work with the latest version of Wine. Older versions are available in the Wine archive.
You might also have a problem, because you are using Ubuntu. There are many Ubuntu fans, but to be honest, Ubuntu is not a very good system. I tried to play a game on Ubuntu using Wine, but the game was unplayable: slow, skipping, bad sound. The same game and same version of Wine on Debian worked almost perfectly.