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A highly underappreciated game by this crowd (IMO) remains Baseball Mogul. Yes, it still has its quirks, but it's a highly flexible, speedy, accurate enough, and most important, lots of fun.
Another vote for Omni-Play/Magic MVP Basketball. The game was ahead of its time and I still miss some features of it (like the commercials, detailed team vs. team comparisons, and trading/development "points").
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