Your problem lies

In your ripping software. There should be, clearly marked someplace, an option to number tracks as they are ripped. Have you scoured all of the deepest reaches of Music Match for such an option? I used media jukebox for my ripping tool. I think it's no longer freeware though, and quite a rescource hog. Good luck. Ohh, and have you checked winamp 3 beta? I think it's got a ripping utility now.