First of all, that is the way it is at all tournaments. You will see the better kids in any bracket get more matches so they have a better chance at OW. Second if you lose and go out the back side you are not eligible for the OW trophy. The trophy only goes to a champion.
Thanks for the congratulations and I hope your son has a good year. If you have any questions on how it all works you can contact me at brimisand7@sbcglobal.net.

Thanks Again
Brian