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It uses matches based on the same Song and Artist, although you will see multiple versions of the same song from different albums.
Step 3: Select the Advanced tab in the i Tunes Preferences window.
Go through the tracks and remove any duplicates you don't want.
Highlight the unwanted file, press Delete on the keyboard (or choose Edit Delete) and select Move To Trash.
Click "OK" to import all songs from the i Tunes Media folder into Windows Media Player.
The "Update Media Library" message is displayed in the bottom right corner of Windows Media Player until all media files are imported into the library.
i Tunes no longer imports duplicate files if you drag-and-drop audio files to the i Tunes library (you can force it to add the duplicate file by holding down the Option key while dragging the file). However, it is a good idea to double-check that i Tunes is managing your music files correctly.