I had to check on my own as I never tried this scenario.
It looks like Addressable doesn't treat these two uri's as equal and Webmock depends on Addressable,
when comparing uri's.
rfc 2396 states that "The path may consist of a sequence of path segments separated by a single slash "/" character."
It wouldn't really be a problem to add logic to Webmock which would remove double slashes.
Not sure if it should either.
Bartosz