To start 1-3 and win the top seed is one hell of a job. I am going to bet no team in Ivy history has done that and won the title.
Closest might be ‘02 when Penn started 2-3 and ended up with the bye in the three-way playoff after tying Princeton and Yale, because they had swept PU and ended 3-1 against the other two.
In that 2002 season recalled by Chip, after Penn started 2-3, Penn needed to run the table. They finished the season 9-0 to create the three way tie at 11-3.