Microware, having apparently so carefully followed the letter of
trademark law with respect to AT&T Unix, sued Apple for peddling "OS/9"
in the operating system market, and promptly got their asses handed to
them by the federal district court, which dutifully honored the foremost
principle of law: big people get to stomp smaller people as often, and
as hard, as they would like.[2]
To be fair, the judge decided that there wasn't a whole lot of risk of consumer confusion between a consumer OS that ran only on Apple Macintoshes and an OEM OS that did not. The only actual victims were Mac people who stumbled into comp.os.os9 and got seriously confused.
In any case, Microsoft v. Lindows pretty much established that sometimes the little guy wins, even in trademark cases. Microsoft claimed that Lindows was infringing their trademark for Windows (it was a Linux distro that came with Wine and some glue) and lost the case on prior-use grounds (both Xerox and Apple). So rather than risking all on a retrial and maybe losing the Windows trademark altogether, they settled for US$20M and Lindows changed its corporate and distro names to Linspire.
That said, "Windows" is a descriptive trademark, and those are always shaky legally.
Cisco rolled over
and took some undisclosed amount of money,
Money undoubtedly flowed from Apple Computers to Apple Records when the first company started selling music, too. This sort of thing is routine. While I was working at Chase Bank, they paid a small fortune to Chase Research for the rights to "
chase.com".