Hard to say. Newer operating systems may not be compatible with games that have been coded for older OS. The oldest game I played recently on a modern laptop with Windows 8.1 is Elder Scrolls III: Morrowind which I think was released back in 2001. I had no issues with it.
However, games like the Sims 1 and Sims 2 do not appear to be compatible with Win 8 from what I have read. But EA released an "Ultimate Sims Collection" where all the Sims games are compatible with Win 8 / Win 10.