Are you using either iTunes Match or Apple Music? These have features that prevent duplicates being added to the iCloud Music Library. Other than that iTunes should allow you to create duplicates if you import the same media from outside the media folder and iTunes is set to make copies inside, or you copy the same set of files into the Automatically Add to iTunes folder, or rip the same CD more than once.
What exactly are you trying to achieve? Duplicates at different bitrates/formats or multiple copies of a track in a playlist, or something else? To the best of my knowledge iTunes has no features for actively eliminating duplicates.
tt2