iTunes Match

I've spent the better part of a day trying to figure out the same thing and haven't had any luck. I'm so ****** I'm killing iCloud and the evil Match all together.

Yes, you can either initiate the download from match to your phone right on the phone in "Music" where the music is listed. When looking at the list of music available to play in match on your phone. Look on the right side, there should be an icon of a cloud with an arrow pointing down. By clicking that, you will download the song to your phone allowing you to play the music then match isnt available. I think you can also connect your phone to itunes and move the songs to your phone there as well. Having the music loaded on your phone is important if you want to play your music when you dont have data connection. Honestly, even with a data connection i find match to be very glitchy. Hope they fix it because it is a good concept.

...and, a year later - we're still pretty glitchy with iTunes Match. It was working really well before Yosemite came out. Now, I feel like we're back to square one.