Right now, it's very common for the role of Prince Orlofsky in Strauss's operetta Die Fledermaus to be played by a woman, though it's also played by some tenors. In the nineteenth century, 1865 or thereabouts - especially at a prestigious performance in Vienna attended by the Imperial couple - would the role of Orlofsky still be played by a woman?
EDIT: Answered, but I have a further question - are there any other operas/operettas with swaggering (borderline) comedic "trouser roles" like that? I'm not sure if Cherubino in Le nozze di Figaro is quite what I'm looking for.