Since the time I got my 160GB iPod classic I started scrobbling, sending all the songs played while on move to my last.fm profile. However since the beginning I had an issue once in while, or many times in the row, when I was syncing iPod with iTunes all my plays where missing. I tried various solutions, one part was avoiding iTunes and windows all over and scrobbling with a linux virtual machine, through the linux version of the last.fm player. Still it seems that the problem persisted.
After a while I discovered that the iPod actually kept play counts and last played dates, but some how iTunes or the last.fm player actually failed to recognize them and they where deleted during the sync process. The solution was accidentally found through the usage of MusicBee. Since the play counts are stored in the iPod there must be probably some inconsistency in the iPod DB that causes the issue. So a workaround is to play a track from the iPod music library with MusicBee, this seems to fix the issue, because afterwards the linux last.fm player gets every single played track in the list with the tracks to be scrobbled.