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.
Apple sued Microsoft on 189 counts of copyright infringement relating to Windows 2.0.3. The judge overseeing the case throws out 179 of them. This paves the way for Microsoft’s dominance over Apple in the coming decade.
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
Apple CEO John Sculley and Macintosh boss Jean Louis Gassée ignore the advice of the 30-year-old Gates, who at the time is best known as a Mac developer. Five months later, Microsoft releases Windows 1.0.
May 26, 2010: In a massive milestone, Apple passes Microsoft to become the world’s most valuable technology company.
The changing of the guard proves particularly amazing given that, just 15 years earlier, Apple looked close to dead, while Microsoft dominated the tech world thanks to Windows.
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.
The reason? Mobile phones are going to steal the iPod’s market share. The good news for Gates is that he was right on the money. The bad news for Microsoft is that Apple cannibalized itself by making the iPhone. And Apple’s smartphone became even more successful than the iPod.
April 4, 1975: Childhood friends Bill Gates and Paul Allen found Microsoft Corporation, a software company destined to become a tech behemoth — and a major Apple frenemy.
A few years later, Microsoft will break through to the mainstream with Excel and Word, becoming a key developer of Macintosh software. Then comes the Windows operating system, looking suspiciously Apple-like. After that, Microsoft and Apple will embark upon a long-running feud.
March 17, 1988: Apple sues Microsoft for allegedly stealing 189 different elements of its Macintosh operating system to create Windows 2.0.
The incident, which causes a deep rift between Apple and one of its top developers, paves the way for an epic battle between the two companies that will rage for years.
February 11, 2010: With iPad excitement reaching a fever pitch, Steve Jobs’ old frenemy Bill Gates wades in with his own opinion of Apple’s tablet.
His view? It’s kinda meh.
“There’s nothing on the iPad I look at and say, ‘Oh, I wish Microsoft had done it,'” he tells one interviewer.
January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates steps down from his role as Microsoft CEO, a month after his company’s stock hit its all-time high.
The news coincides with a turning point in the long-running battle between the two tech powerhouses. Microsoft begins a long decline from its previous dominance, while Apple continues its rise to the top.
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 its all-time high of $53.60, Microsoft stock starts to fall. Less than a year later, Microsoft shares 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,” claims Microsoft co-founder Bill Gates in a BusinessWeek cover story.
The claim would seem almost unthinkable coming out of Gates’ mouth just a few years later. But it comes at a time when Microsoft is best known as one of the biggest Mac developers.
