I see this hilarious scenario: GenericOpenTeam signs up early and a few days later GreatTeam puts themselves in the same opening round. Worried, GenericOpenTeam moves to another open bracket and is thusly followed by GreatTeam. A few times. Until there is nowhere left to run and GenericOpenTeam is forced to play a different GreatTeam, in a sense being punished for signing up early.
Eventually, teams are continually trying to "beat the clock", much the same way as bidding on a hot item on eBay (refreshing your browser every few seconds until you finally hit submit). No one signs up until the last minute, resulting in some interesting cross-edits. In the end, clan-mates GoodTeamA and GoodTeamB pull a last second switch, which leads one of them to a Ladle victory. Participants feel swindled, and 6 fiery pages get added to the Ladle thread (and two 1-week bans while we're at it).
Ideally, teams will voluntarily pick opponents of equal skill level to play because it's more fun. That would be a lovely reality. But there are always those for whom winning...is...EVERYTHING.