Hello CTGame,
Welcome to Apple Support Communities.
It sounds like there’s a grayed out song in your iTunes library that can’t be played or downloaded again like other past purchases. Try taking a look at the article linked below and verify the computer is authorized to play that content.
How to troubleshoot iTunes Match - Apple Support
Songs appear to be missing
Songs containing DRM (Digital Rights Management) might not appear in iCloud, or might appear grayed out. This can occur if your computer is not authorized to play that content. Try authorizing your computer, then manually update iTunes Match. To determine what Apple ID your computer needs to be authorized for to play a specific song:
- Locate and select the song in your iTunes library.
- Choose File > Get Info.
- In the Summary tab, locate the Account Name field in the right column. Write it down.
- Click OK.
- Choose Store > Authorize this Computer.
- Type in the account name from the Summary field and enter its password. Click Authorize.
- Choose Store > Update iTunes Match.
So long,
-Jason