I don't think you should count what happens in the game itself. For me, good or bad cup draw is all about lineup planning for the week. It doesn't matter if you get CT'd if you win.
I suppose the issue between getting out-efforted is if they have a track record of doing it in the past. If yes, then that factors into lineup planning for the week, since you need to be wary of such a threat.
I guess maybe there could be some retroactive stuff. If Technical Fouls CTs me and knocks me out, does that make him a worse draw than Quakers drawing Bruins? I don't think so, since one of them loses too.
I'm leaning towards it only affecting lineup planning, so not retroactive. The team Bruins played did not have much of a Cup History at all, and anytime he went to the round of 128 or even 256 was when he had very favorable draws.
I think the only way a retroactive (worst cup draw) adjustment would be made is if the opponents are from the same division.
I'm fine with Quakers and myself getting a tie for that round, since after the Saturday game, it looked like both of our opponents were aiming to steal the Cup game. So that can still change your lineup plans for the Tuesday game.
But it could work as a tiebreaker?
I think the best tiebreaker would be just counting up D2 opponents for weeks you didn't have the worst Cup draw. KDB probably has the edge in that area.