How to Match songs in your library to Apple Music library?

What is the cloud status of the tracks when you look at them in a Songs view or playlist? E.g. Matched, Waiting, Duplicate, etc. Right-click on the column headings to add the Cloud Status column if needed.

tt2

Make sure the original track is download to your library and backed up. You can then try holding down Option as you launch Music to create a new empty library, then delete one of the affected tracks from the new library, close Music and switch back to the original library. The track should now show as removed. You can either try right-click add to library to see if it will add back in and match, rather than upload, or you can add the track in question directly from Apple Music. Matching is supposed to be done on the basis of audio fingerprints, but it may still help if your metadata agrees with the store. Assuming you can get it to work with a single track and Music retains the play counts you can try with some larger batches.

tt2

As noted:

Make sure the original track is download to your library and backed up.

When you revert to the original library where the content is stored locally the specific track that you deleted should now have a cloud status of Removed, which will give you an opportunity to add it back to the library. This should also be a track that is available in the Apple Music collection if you were to have any chance of having it match instead of upload. At worst you should be able to add it back directly from Apple Music, the issue is whether or not it will merge the play counts from existing entry.

tt2

Ah, you would need to enable Sync Library, aka iCloud Music Library, to show your cloud content associated with the subscription.

tt2