I asked Matt, and it's pretty simple - the client looks for <file name>.bz2 first, before looking for the original file.
So grab a compression app (I work from an OS X box, so I just use 'bzip2' from the shell...) compress the bsp, and move up the map_name.bz2 to the maps directory on the web server.
If you're on linux you've got bzip2 as well. On windows, there's a bzip2 command line util: http://gnuwin32.sourceforge.net/packages/bzip2.htm
I'm sure you can find a bunch of GUI compression apps for windows which support bz2 with a little legwork.
-b
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