There will be a new trophy. People will over think it and come up with some thing crappy like a replicated rock from the 1800's.
It should be the same trophy just replaced with the modern Bison logo on one side and the Fighting Hawk logo on the other.
This perfectly mixes the old with the new and keeps some historical significance in the new trophy.
The one who's team goes further in the (non loser bracket) season duh. Thats sort of how sports work.
Brewster doesn't even have to face any schools top sports team like Jones has to. That gives Brewster like 8 free wins a year.
Jones can walk into Hyslop tomorrow and brag to Brewster about how his team went further than his last year.
....and then say, "Oh yeah and the year before last year too!"