please see this Apple help entry on the Matched status:
Note that Matched means, iTunes is working with a “Matched” duplicate from Apple Music, not your local file.
Unfortunately there is no way for 3rd-party DJ style apps such as djay to play songs from Apple Music, Apple’s music streaming service. This also applies when songs are downloaded onto your device from Apple Music, as the downloaded files will be DRM-protected.
Could you try to delete the track of the My Library playlists and add the same track via drag and drop to the playlist directly from iTunes?
After doing so, does the error persists?
Also are the tracks referring to the same track when you look for them in the finder?
If you have any questions or suggestions, or if you would like further information, please don’t hesitate to contact us.
My issue is that they play perfectly fine when I chose to play them from within the iTunes tab in Dj Pro 2 but refuse to play if I play them in My Library/History.
So we are not talking about matched items then but rather unmatched ones. Locally, not copyright protected ones.
So, here’s another example of something feeling wonky and unpredictable in regards to tracks not being reliably found.
In this case the reference from DJ Pro’s internal playlist seems broken and I cannot load the track but when I try to load it from the internal Itunes search function/librarry it loads without problems.
That’s so bizzare as it is 100% reproducible over here.
I recorded a video and put it up in this thread after your reply in regards to matched and bought songs. Please have a look at it as it will show you the issues in question, and yes, also that it’s pointing to the right file.