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Here are some Knowledge Base articles from Microsoft that can help you troubleshoot MS-DOS based games and 16-bit Windows applications.
KB articles related to MS-DOS based games
An Error Message Is Displayed When You Attempt to Install or Remove or Play a Game Programs that Require OpenGL Support May Not Run in Windows XP Resources for troubleshooting games and multimedia in Windows XP Cannot Use DirectPlay Programs on the Internet After You Install Windows XP SP1 Game stops responding (hangs) or quits unexpectedly when introductory video clip is played
KB articles related to 16-bit Windows applications Virtual Device Driver Error Message in 16-Bit MS-DOS Subsystem Troubleshooting MS-DOS-based programs in Windows XP "16 Bit MS-DOS Subsystem" Error Message When You Install a Program How to Troubleshoot 16-Bit Windows Programs in Windows XP HOW TO: Identify a 16-bit Program in Windows XP Error message when you install or start an MS-DOS or 16-bit Windows-based program