I'm not sure if this is possible. I have some old CDs in my attic. I'd like to use them with iTunes match also. Do I have to rip them first, or does iTunes match recognize you own a legit CD and match it automatically? This if possible would save tons of time. Im just thinking that has to be just as legit as it isif someone ripped all their CDs. Just thought I'd ask before spending days working on this.