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 deal, between 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.”

Oh, boy!

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 before Apple launches the Mac in 1984, Windows 1.0 won’t actually ship until November 1985, earning it a reputation as “vaporware.”

At the time, Apple doesn’t view Windows as much of a threat. That doesn’t take long to change, however.

Thanks to cooperation between Apple and Microsoft, the Windows 11 Photos app is now able to access photos and videos from iCloud.

This is one of several recent cross-platform collaboration moves by the two tech titans.

November 6, 2003: After porting iTunes to Windows, Apple sets a new record for digital music sales: a massive 1.5 million downloads in one week.

Bringing iTunes to PC users opens up a new, lucrative market for Apple. The record-breaking sales clock in at five times more than the 300,000 downloads Napster (remember it?) achieved in its debut week. And 1.5 million is double the 600,000 iTunes downloads per week Apple reported selling to Mac users prior to the Windows release.

October 16, 2003: Six months after opening the iTunes Music Store for Mac owners, Apple expands the service to cover Windows PCs as well.

Apple CEO Steve Jobs later quips that making iTunes available to Windows owners is akin to “giving a glass of ice water to somebody in hell.”

Microsoft and Apple are cooperating to enable the Windows 11 Photos app to access photos and videos from iCloud. In addition, the Apple Music and the Apple TV applications are also coming to Windows.

The Apple vs. Microsoft war is truly over.

Real-world experiments with the new MacBook Air show Apple’s latest can use Parallels 18 to run Windows 11 faster than a Dell XPS Plus.

It’s a tribute to the performance of the Apple M2 processor in the latest Air.

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.

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.

June 11, 2007: At WWDC, Apple CEO Steve Jobs unveils Safari 3 for Windows, bringing the company’s web browser to PCs for the first time.

Apple pitches Safari as the world’s fastest and easiest-to-use web browser, capable of rendering web pages up to twice as fast as Internet Explorer and 1.6 times faster than Firefox. Safari for Windows lasts until 2012, but never becomes a major player on Microsoft’s dominant operating system.

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