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.
November 26, 1984: “The next generation of interesting software will be done on the Macintosh, not the IBM PC,” predicts Microsoft co-founder Bill Gates in a BusinessWeek cover story. Gates’ praise for the Mac would seem almost unthinkable coming out of Gates’ mouth just a few years later.
November 21, 1985: Following
August 26, 1991: In their first joint interview, Steve Jobs and Bill Gates trade barbs and debate “the future of the PC” in Fortune magazine.
August 21, 2008: Microsoft recruits comedian Jerry Seinfeld for a series of ads. It’s a naked attempt to shake the company’s reputation as a stodgy oldster (as opposed to Apple’s trendsetting hipster image).
August 6, 1997: In one of the most famous moments in Apple history, Steve Jobs reveals a $150 million Microsoft investment that saved his company from ruin.
July 25, 1989: Apple suffers a major setback in its copyright-infringement lawsuit against Microsoft for allegedly stealing the Mac’s “look and feel” to create Windows.
June 25, 1985: Microsoft co-founder Bill Gates sends a memo to Apple execs suggesting that Cupertino should license its Mac operating system and additional technology to other companies.
May 26, 2010: In a massive milestone, Apple passes Microsoft to become the world’s most valuable technology company.
May 12, 2005: Longtime Apple frenemy Bill Gates tells a German newspaper that Apple may have hit it big with the iPod, but that its success isn’t going to last forever.
April 4, 1975: Microsoft is founded by childhood friends Bill Gates and Paul Allen. The software company destined to become a tech behemoth — and a major Apple frenemy.
March 17, 1988: Apple sues Microsoft for allegedly stealing 189 different elements of its Macintosh operating system to create Windows 2.0.
February 11, 2010: With iPad excitement reaching a fever pitch, Steve Jobs’
January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates steps down from his role as Microsoft CEO, a month after his company’s stock hits its all-time high.