Q: How can I safely delete songs from my iTunes library to save space after subscribing to iTunes Match?

Hello Joesullivan3rd,

It sounds like you want to be able to delete music you have in your iTunes library to free up room on your computer so you can stream them from iTunes Match. You can use these steps to delete the music:

1. Launch iTunes.
2. From the Library pop-up menu, choose Music.
3. Click Songs in the navigation bar.
4. Click the song you want to delete.
5. Press the Delete key on your keyboard.

In iTunes 11, the album cover art will remain visible, but a cloud icon will appear on it to allow you to download the item again (in countries that support this).

How to delete content you've downloaded from the iTunes Store, App Store, iBooks Store, or Mac App Store

http://support.apple.com/kb/HT5772

When you delete them, you will see the following window pop up from the article:

iTunes Store: How to delete songs from iCloud

http://support.apple.com/kb/ht4915

Uncheck the check box that says "Also delete this song from iCloud" and that will keep your music in the Cloud, but remove the file from your library.

If you would like you can ensure your library against any mis haps by backing it up:

iTunes: Back up your iTunes library by copying to an external hard drive

http://support.apple.com/kb/ht1751

Thank you for using Apple Support Communities.

Cheers,

Sterling