ITunes Match and iPod Classic sync problems

Hi all,
I've recently signed up to iTunes Match and use iTunes on my Windows PC (at home) and MacBook Pro (at work). I also use an iPod Classic which I sync with the Windows PC.
I've had an issue which has happened a few times when I sync. I think the problem occurs when iTunes is open on both the PC and the Mac, but I'm not sure.
When I sync my iPod, it increments play count, and updates the recently played playlist as normal, but every now and then, I am asked to sign back into iTunes Match, and when I do that, all play counts from the ipod sync disappear. The Recently Played playlist also no longer has songs played on the iPod included. However, on the "last played" field, the correct date and time of when the song was played in populated.
The iPod is where I listen to music most often, and I would really like to keep the play counts up to date, but I can't figure out what is happening.
Has anyone seen this before? Any ideas if I can resolve this?
Thanks.

The same thing happened to my iPod. It shows that it has no songs, but when i checked the iPod's memory, it was using the same amount of space as before (i had 52 gb of music, now it's just 52 gb of... nothing).

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