Grouping Movies in iTunes

Sounds like you're working with TV shows.

If that's the case, you can right click on your file, go to "Get Info" and fill in the details there. The most important for you would be the 'Video' tab, then click on 'Video Kind' and select the 'TV Show' drop down. Fill in season number and episode number/id along with the name and it'll start to sort itself.

That's the long way around. There are programs which will help fill this information in for you. On the Mac, Metax is a good one. Not sure of Windows alternatives.
 
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