Blast from the past
"Play Your Favorite DOS Games in XP, Vista, and Windows 7". X-Com, Lost Admiral, Pizza Tycoon, and Wayne Gretsky's Hockey would be worth playing again.
Or if you'd rather spend time with things that are more up-to-date, you could try "The greatest internet sports games of all time". "Quick Hit Football" looks interesting, but I haven't spent much time with it.