I recently noticed that my iPhone 4S with iTunes Match enabled is no longer updating play count and last played when syncing with iTunes. The iPhone is not my primary iPod, but I do use it on occasion and I do have a Smart Playlist that uses play count as criteria.
iTunes Match is actually supposed to sync play count information from your iOS device to your Mac. Unfortunately, in our experience, this syncing has been rather hit-and-miss, with the play count not always being updated in a timely manner. We have a couple of suggestions: Make sure that iTunes and iOS have been updated to the latest version.

A quick troubleshooting step is to disable iTunes Match, and then re-enable it.
Secondly, try disabling and re-enabling iTunes Match on your iOS device. You can do this by heading to Settings > Music, and turning off iTunes Match.
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