I feel like it's fairly unlikely, mostly because Doben doesn't seem to be the type of guy who would accept a draw in these circumstances. He may have more respect for Waffles now than in the previous iteration of the cycle, but he's still ultimately out to prove that he's the best candidate to be the Hero. He'll accept victory, or he'll accept a fair loss, but a draw? Not happening.
Likewise, in this new iteration of the cycle Waffles is a lot stronger, but more importantly, more confident in himself and his ability. So he's just as invested in Doben, and also unlikely to accept a draw.
I wouldn't object to them teaming up after settling the question of who's strongest, and now that there's a chance for them to establish a bond of trust and mutual respect, that feels like a probable outcome. But if the manga is going to buck the "only one Hero allowed" trope at some point, I don't feel like it'll happen here just because of how much else is already going on in this arc.
