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What sort of playlist? Music or Podcast? I ask because I lost a favorite playlist that is of smart type and Podcasts moving to Match and did not get it back when switching phone from Match. It shows under the phone in iTunes but not as a play list on the phone.
I do see some of my music playlists in iTunes did not sync but the tracks in the lists did.
Actually it was all of them; genius, smart, and the ones I made. They initially transferred, but I redid the match and they didn't show up on my i-pad the 2nd time around.