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Jun 20, 2016 8:19 AM in response to Chris Hiteby turingtest2,★HelpfuliTunes can only transfer content that is stored locally to your iPod classic, so you'll need to download the music first. If you have iTunes Match you don't need to build a new library, since I assume you can already see your matched content. If the issue is not having enough room to download the media before transferring it to the iPod take a look at Make a split library portable. Ideally you would maintain a one local copy, and a backup, over and above iTunes Match in case of a mismatch, library corruption, and/or for content that cannot be added to Match.
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