It's difficult for Apple to match songs that were ripped from CD because of the lack of ID3 tags. Macworld has a great article on the Secrets of iTunes Match. Apple does not do a very good job of documenting how iTunes Match actually works, although WordsWorth in the chatroom pointed to an Apple discussion about Troubleshooting iTunes Match. If Chris has the full album with proper tags, it'll do a better job. He also should make sure the quality of the songs are 96kbps or higher. If the songs aren't, then he can re-encode them through iTunes to a higher quality.
There's a way Chris can find out what iTunes Match did with each song. Right click on the top bar in iTunes, and select "iCloud Status". This will let him sort his library based on whether songs were matched or just uploaded. It isn't uncommon for iTunes to not recognize songs and upload them instead, and in fact Leo has quite a few songs that were uploaded instead of matched as well.