November 10, 1983: Microsoft tells the world about an upcoming product called Windows that will bring the graphical user interface to IBM PCs. Although Microsoft’s announcement about the new operating system comes shortly before Apple launches the Mac, Windows 1.0 won’t actually ship until November 1985, earning it an early reputation as “vaporware.”
At the time, Apple doesn’t view Windows as much of a threat. That doesn’t take long to change, however.
September 11, 2009: Microsoft CEO Steve Ballmer snatches an iPhone from an employee during a meeting and pretends to destroy it.
The iPhone freakout isn’t the first time Ballmer behaves in a wacky way and incurs negative publicity as a result. However, it’s an embarrassing moment for a man who ranks among the tech world’s most powerful people.
September 6, 1995: The newly launched Windows 95 operating system dominates software sales, sending virtually every other company scurrying for cover — Apple included.
After launching Windows 95 at the end of August, Microsoft sells a massive 1.63 million copies of the $85 PC operating system by early September, according to excited analysts. It represents a massive triumph for Apple’s biggest rival of the 1990s.
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).
Microsoft pays Seinfeld a reported $10 million for the ads. However, thanks to the Mac’s appearance in virtually every episode of Seinfeld over the years, the comedian remains the world’s most famous Apple fanboy.
August 14, 1991: As Apple and Microsoft head to court to battle each other, the tide begins to turn against Cupertino and its claims that Windows unlawfully copies the look and feel of Mac OS. A judge’s ruling calls into question the basic tenet of Apple’s copyright lawsuit against Microsoft over Windows 2.03.
The case concerns whether key elements of Apple’s operating system are original enough for copyright protection. The decision turns out to be a major blow against Apple — and the start of the company’s 1990s decline.
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.
Although often presented as an inexplicable gesture of good faith on the part of Microsoft boss Bill Gates, the cash infusion into Apple actually benefits both companies.
May 26, 2010: In a massive milestone, Apple passes Microsoft to become the world’s most valuable technology company for the first time.
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 95.
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April 16, 2009: Apple hits back at Microsoft following an advertisement that criticizes Cupertino for failing to sell decent laptops for less than $1,000.
“A PC is no bargain when it doesn’t do what you want,” Mac PR director Bill Evans tells Bloomberg. “The one thing that both Apple and Microsoft can agree on is that everyone thinks the Mac is cool. With its great designs and advanced software, nothing matches it at any price.”
April 5, 2006: Apple introduces the public beta of Boot Camp, software that allows users with an Intel-based Mac to run Windows XP on their machines.
Boot Camp will officially arrive in Mac OS X Leopard, which debuts at Apple’s Worldwide Developers Conference a few months later.
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.
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 Windows arrives, Microsoft and Apple will embark upon a long-running feud.
April 2, 1980: Microsoft releases its first hardware product, the Z-80 SoftCard. A microprocessor card that plugs into the Apple II, it allows the computer to run programs designed for the CP/M operating system, a popular OS for business software.
Arriving several years before the first version of Windows, the Z-80 SoftCard quickly becomes a big hit for Microsoft.
February 14, 1995: Apple Computer extends a lawsuit against developer San Francisco Canyon Company to include Microsoft and Intel. The lawsuit concerns allegedly stolen Apple code that’s used to improve Microsoft’s Video for Windows technology.
The lawsuit comes to a head with Apple threatening a multibillion-dollar lawsuit against Microsoft. Meanwhile, Microsoft CEO Bill Gates threatens to cancel Office for Mac.
February 11, 2010: With iPad excitement reaching a fever pitch, Microsoft co-founder Bill Gates wades in with his opinion of Apple’s tablet. His view? Apple’s upcoming device is kinda meh.
“There’s nothing on the iPad I look at and say, ‘Oh, I wish Microsoft had done it,'” Gates tells one interviewer.
February 4, 2008: Apple CEO Steve Jobs reportedly considers buying the search engine Yahoo. Apple is one of several interested companies, following reports that Microsoft offered $44.6 billion for the web portal the previous week.
Nothing ultimately comes of it, but Apple’s interest is later confirmed in an authorized biography of Jobs.
January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates quits as Microsoft CEO. He steps down from the leadership role just 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 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.
Microsoft started rolling out an upgrade Wednesday to its Phone Link software and the Link to Windows app that promises seamless file transfers from iPhone to PC and vice versa.
The goal seems to be imitating the functionality of AirDrop, Apple’s simple system for wirelessly moving files between iPhones, Macs, iPads, etc.
November 21, 1985: Following Steve Jobs’ departure, Apple comes close to signing its own death warrant by licensing the Macintosh’s look and feel to Microsoft. The Apple-Microsoft deal — struck by Microsoft co-founder Bill Gates and Apple CEO John Sculley — comes hot on the heels of the Windows operating system’s release.
The pact gives Microsoft a “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs, and to license them to and through third parties for use in their software programs.” If you’re wondering when did Bill Gates step down as CEO, his departure marked a major shift in Microsoft’s leadership.
Oh, boy!
Apple relaxed the App Store rules earlier this year, paving the way for cloud gaming apps on the iPhone. However, Microsoft and Nvidia have not yet listed their cloud gaming services on the App Store. The former argues that Apple’s rules are still too restrictive for this.
Microsoft’s main issue revolves around the 30% commission that Apple wants for IAPs. It says the fee is “neither economically sustainable nor justifiable.”
With a market capitalization above $3.6 trillion, Apple regained the title of world’s most valuable publicly traded company. The Mac-maker is valued well above Microsoft and Nvidia, both of which had been valued higher earlier this year.
A recent sharp rise in AAPL share value seems to indicate that investors are optimistic that a surge in iPhone sales is on the horizon.
Starting in September, Microsoft will require its employees in China to use iPhones for work-related activities, effectively banning Android devices from work use, according to a new report. And of course the irony of a new policy stating that Microsoft employees in China must use Apple devices isn’t lost on us.
Apple rose to once again become the world’s most valuable publicly traded company on Wednesday. Its market capitalization passed $3.3 trillion, once again putting the Mac-maker ahead of Microsoft.
This comes just days after Apple dropped to third place when Nvidia’s share market cap briefly rose ahead. But AAPL has been on a tear since announcing plans this week to integrate AI into iPhone, Mac and other products.
Update: Stocks go down as well as up, and when Wall Street closed on Wednesday, Microsoft’s valuation was slightly higher than Apple’s.
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When it comes to deploying artificial intelligence in products, companies like Google might seem quicker on the draw than Apple. But no major tech company bought more AI startups than the iPhone-maker in 2023, according to a new report.
That suggests Apple might soon become a leader in generative AI rather than playing catch-up.