Tired of seeing duplicate tracks in your iPhone or iPod and starting your playlist to find the same songs playing over and over caused by duplicates. If the only problem is duplicate tracks in iTunes library and not duplicate files in your drive then here's a trick to remove all duplicate tracks in your iTunes media library then synchronize it with your device again.

Manual Solution:

1. Use iTunes built-in “Find Duplicates” feature to find the duplicate tracks in iTunes. – (this doesn’t affect your drive yet).
2. Highlight the resulting tracks in your iTunes Library and then drag the tracks from iTunes to a new Folder on your drive.
3. This will make a complete copy of your Library (without any duplicates)
4. Delete every track in iTunes and every file in your original Library on your drive.
5. Then, either move the contents of your new Folder to your Library folder and drop the Library Folder back into iTunes, or just tell iTunes that your Library has moved to the new Folder.

You’ll now have a new Library with no duplicates.

However, if the *files* (on the hard drive) are duplicated (because of different folder/file names), then the solution is tedious and requires a lot of temp disk space.