ICloud – On iTunes for Mac, download all music from iTunes Match

You may not be able to get complete matches, but here's what I have been doing in the cases where one or two tracks don't match.

1. Select the item(s) to attempt to re-match.
2. Right-click on them, and select "Create AAC Version"
3. When this is complete, hit alt-backspace, and choose to remove both the original and the iCloud version. Also choose to delete the items from disk.
4. Go to the "Store" -> "Update iTunes Match" menu item.

Note that this will keep the play counts, etc on your tracks. It may not succeed on every track, and sometimes repeating the process picks up another track.

Occasionally, I'll get a "Removed" icon there after doing this: just right-click and choose "Add to iCloud" on these.

I would export a copy of those songs to a folder in /Users/Shared and then turn off iTunes Match. Then:

1. Make a new user on your Mac
2. Log out of your existing user
3. Log into this brand-new user and fire up iTunes

It should have no music whatsoever and not be linked to your Apple ID. Now go ahead and sign into iTunes match and see what the cloud really thinks your music library looks like. Drag one and only one song from the users/shared folder into this library and leave iTunes running for a while to see what iTunes match makes of it.

At that point you have a very isolated and potentially reproducible issue that you could reach out to Apple support in case the problem is on the server side and nothing that you were doing.