There was once a time when the two tech giants squared off in court. Apple filed a lawsuit against Microsoft in 1988, shortly after the release of Windows 2.0, a significant upgrade to the original version.

At the time, Apple accused Microsoft of plagiarizing the graphical user interface found on the Macintosh system without permission or a license. This is where the case becomes interesting, as Apple did in fact grant Microsoft permission to use Macintosh’s design elements in Windows.

The mystery surrounding this part is that, for some reason, Apple’s legal department did not receive the memo, after the release of Windows 2.0, Apple was so taken aback by the suddenness of the legal proceedings that it skipped sending any sort of preemptive warning or threat.

As a result of this misunderstanding, the court ruled in favor of Microsoft in 1989, and although Apple attempted to appeal the decision multiple times, all of its efforts were unsuccessful.

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