I'm not enough of a history boffin to know how Microsoft came to support it differently (perhaps something from the Netbios and NT era). At this point in time though, I don't see either party changing their default validations to agree on a single definition.
Edit: If you're curious, this is the first commit that appears to be the first glibc commit limiting dashes at the end of URLS https://sourceware.org/git/?p=glibc.git;a=commitdiff;h=fa0bc.... I don't know about BSD libc, or windows however.