It's been running for about 1.5hrs, 8259 out of 13172 songs matched. I have 15,828 files in my iTunes Music Directory. So iTunes Match was unable to find 2656 files and these 2656 files will be uploaded into the cloud. Update: Started at around 6pm took a nap and forgot about it. Woke up at about 12am and it was done. So I'm guessing for 15,828 files, it took between 4 maybe 6 hours?