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Create a smart playlist with songs that have a playcount of less than 1, then you can put that on shuffle and it will play through those songs.

Alternatively, sort your library by playcount (in View- Options) if the column isn't there yet, take Shuffle off - and just play through the ones that are blank
 
How do I create the smart playlist? I already made a new playlist, so now what?
 
Go to the File Menu, choose New Smart Play List

iTunes will pop up a dialogue box. From the drop down list, choose Playcount and then set your criteria. Make sure smart updating is selected and then hit OK

Give it a name like - 'unplayed tracks' and you're good to go
 
Thank you, I clicked shuffle, so now it will just shuffle on this playlist? I have about 100 songs out of 4k that haven't been played yet.
 
cmm said:
Thank you, I clicked shuffle, so now it will just shuffle on this playlist? I have about 100 songs out of 4k that haven't been played yet.
Yes, it will shuffle that playlist. But if you selected "live update", the number of songs in the playlist will eventually reach zero.
 
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