yes, but, it won't automatically replace them.  You would have to first delete 
the old version, then, if iTunes has a match for the song in the iTunes store, 
you would then be able to download it.  Also, after setting up match, it needs 
to upload the songs that iTunes doesn't have, this does take some time.

I have found a few miner glitches where it says it uploaded a song, but either 
didn't get it all or something like that.  
On Nov 18, 2011, at 7:13 AM, Scott Howell wrote:

> Courtney, I do want to download them, so I have access to them when I do not 
> have a network connection. In fact this is one of the advantages of having 
> iTunes Match is the ability to replace lower quality tracks with higher 
> quality versions that you can keep even if you discontinue use of the service.
> 
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