Duplicates in playlist, replacing with non dupe?

I couldn't find the answer for this specifically, but might have overlooked it:
I'm including lots of details about this just to cover all the bases I can to help find a solution.
I recently got iTunes Match to make my life easier, but it's hit hiccups for the last few days, including a gruelingly long upload process. Now that that's done, I decided to put my iPad and iPhone on Match. First, though, I wanted to backup the list of songs on them by making a playlist, in case Match erased the content on them (like it says it will do) and then hits an error.
I made the playlists on the devices, but iTunes wouldn't sync them, nor even show the playlists under the Device>iPad/iPhone tab. It showed other playlists, just not ones made on the devices. I worked around that by selecting all the songs on the devices in iTunes, then made a new playlist on the device from the selected lists, then exported the playlists. When I imported the lists, iTunes said that some songs weren't imported because they couldn't be found.
When I scroll through the list, maybe 100 songs out of the 2000 on it are listed as duplicates with the little cloud-struck-through symbol. Looking through the iTunes library, indeed, these songs are dupes.
However, what I'm needing to do is see if there's an easy way to replace the dupes with their non-dupe brothers before I go through and delete the dupes from my system. I tried a test of deleting a dupe from iTunes and it deleted it from the playlist, too, thus meaning I can't go through and delete all the dupes without losing the song from the playlist. Is there an easy way to batch replace duplicates with the non-dupes? If not, I'll have to go through and manually replace them one at a time, which seems like it ruins a bit of the easy concept of Match.
Any help is massively appreciated. Thanks!

Hi Scott,
When I sync a playlist with duplicates they show up on the iPhone.
Make sure you have the latest version of iTunes and iPhone software.
http://www.apple.com/itunes/download/
http://www.apple.com/iphone/softwareupdate/
-Jason

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Duplicates in playlist, replacing with non dupe?

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