This would be cool but I doubt it'll happen
I think that there could be another bounty room to get bountys for Bosses. For example, If you fight (by fight I mean hitting at least once) the Giant Blob 3 times you get money.
We already have quite a few bosses, like the Flaming Blob and the King Spider. A Gladiator Arena where you can instantly fight bosses with your guild would make Classic tons of more fun. And you'd be able to score points too and get high scores on bosses, and get on the leaderboards, just like Baddy killing, sparring, etc.