December 30, 1999: Microsoft hits the height of its 1990s dominance and begins its early-2000s decline, clearing a gap at the top for Apple.
After hitting an all-time high of $53.60, Microsoft stock starts to fall. Less than a year later, MSFT shares will fall more than 60% in value to $20.
December 29, 1999: Apple starts shipping its unfathomably large 22-inch Cinema Display, the biggest LCD computer display available anywhere,
December 28, 2006: As the rest of the country enjoys a much-deserved holiday, Apple gets embroiled in a stock option “backdating” scandal.

December 27, 2010: Almost four months after the second-gen Apple TV’s debut, Cupertino says it has sold 1 million of the streaming video devices.
December 26, 1982: Time magazine names the personal computer its “Man of the Year.”
December 25, 1977: Steve Wozniak spends the holidays building a prototype of the Disk II, the Apple II computer’s revolutionary floppy disk drive.