Chessmaster 5000, released as the 10th Anniversary edition, introduced a new 32-bit engine, a Windows 95 interface with pop-up menus and long file name support, and a database of over 27,000 games. It features more than ten new 2D and 3D chess sets, over 20 tutorial courses by Eric Schiller, 60+ opening books, 30 new computer personalities, and advanced time controls such as Fischer and hourglass modes. Enhancements include a Coach window, improved annotations with statistics, figurine notation support, and a glossary of over 1,600 terms. Players can compete against the AI, locally, or via remote play.

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