Cannot play matched music on iPhone through Apple Music

I have exactly the same problem. I subscribed to iTunes Match when it first came out to store all my esoteric music and stuff that that was not on Spotify (e.g. Beatles). However, when Google Play allowed the same thing and streaming I cancelled both services. I am now trialling Apple Music and have noticed that all my old Matched music is still there. However, I cannot play it and on iTunes I cannot re-upload it because it says that it is already matched!! I tried to re-purchase iTunes Match because I thought this might be the problem but Apple will not now let me re-purchase it. Thinking of giving up and sticking with Google Play as it just works. The only advantage of iTunes Music is Beats 1 and Family Sharing.

Your situation constitutes what I'm referring to as the "Dual User Scenario" is which your subscribed to ITunes Match and your trying out the new Apple Music Service. Same as myself but I chose to use two separate Apple ID's for each service on each device. Glad I did as I appreciate and understand how it all works. I have a large music library so I rely on iTunes Match. Users with little or no music can solely use the new Apple Music as if represents a Music Rental Streaming service. It's not really a cloud storage and access service like iTunes Match. In your case, your music library was uploaded and matched when you subscribed to iTunes Match. Having now subscribed to Apple Music streaming service, it's assumed all ur music can be matched with the 30 million tracks within the service. In other words, your it really streaming or downloading your personal mystic while using this service. It gets a it more complicated but you could simply enjoy Apple Music and family sharing and consider the iTunes Match as a back up service.

I have the same problem and I tried that described manual fix, but it only worked for about half the affected songs. The others have been stuck in a "waiting" mode for 2 days now -- indicating that iCloud refuses to actually upload them. does anyone have another fix?

yes, i did both (as i thought that might trigger some sort of restart). I mean your approach did allow me to upload some songs, maybe half of the affected items (so many thanks!) but not all of them. can't believe how buggy Apple Music is, i'm tempted to stay with Google Music (even if it doesn't look as nice), Apple's software problems seem to reach the catastrophic levels of Microsoft's products a couple of years ago.