But in a season where little has gone right for the Big Green, the misfortune continued, as Andy Shalbrack picked off Jenny's pass over the middle, securing a 21-13 victory for the Lions.
It was head coach Buddy Teevens' first-ever loss against Columbia (1-5, 1-2 Ivy), as a player or a coach.
With the win, the Lions snapped their 13-game losing streak and extended Dartmouth's (0-6, 0-3 Ivy) drought to eight games without a victory.
The Big Green is last in the league, while Columbia is now in seventh place.
Brown University and the University of Pennsylvania are tied for first heading into next weekend's head-to-head contest in Philadelphia, Pa.
Both teams were forced to battle a driving rain and swirling wind that gusted up to and above 40 miles per hour, breaking many of the umbrellas in the sparse crowd, officially listed at 2,161.
Both teams used two quarterbacks in the game, but it was Columbia that found the mid-game swap to be more effective.
M.A. Olawale replaced Lions starter Shane Kelly with a minute left in the third quarter and completed all seven of his passes while rushing for 52 yards and his second career touchdown.
Jenny, who replaced starter Tim McManus '11, was not as effective. He threw for only 25 yards and an interception after taking over with three minutes left in the third quarter.
"We just weren't as productive as we needed to be, mixing the run and the pass. We needed more productivity in the pass game so we made a shift," Teevens said.
McManus had found some success on the ground, rushing for 28 yards and a score, but was not as productive in the air. He was five for 12 with an interception, throwing for 54 yards in almost three full quarters of work.
Columbia put up 14 points in the second quarter, opening the scoring with a two-yard touchdown run by Ray Rangel.
Dartmouth responded with its only touchdown of the game, and the only points of the game made by a team driving into the wind, when McManus ran the ball eight yards up the middle to tie the game at seven.
The Big Green went 75 yards on 14 plays on a drive that just would not die. Milan Williams '09 ran 22 yards on third down and 12, and McManus set up his score with an impressive pass down the right sideline to Kyle Battle '11 after recovering a fumbled snap.
Columbia responded with a touchdown to go up 14-7 going into the half.
In the third quarter, driving with the wind again, Dartmouth was able to muster just two field goals.
The Big Green's first drive of the quarter stalled on Columbia's 18-yard-line, and its last trip to the Lions' red zone of the game yielded yet another three-point play from the foot of placekicker Foley Schmidt '12.
"We definitely should have gotten more because we started at the 30 yard-line or so," Jenny said of the drive. "That's a situation where the defense makes a great play, and we just need to go down and score, and we couldn't do that."
That field goal brought the Big Green within one, but that was as close as it would get. Olawale came into the game like a shot of adrenaline to the Columbia offense.
"We had guys on [Olawale], non-stop, and just couldn't get him on the ground," Teevens.
Olawale led the Lions down the field twice, once for a touchdown, and a second time to the Dartmouth 19 yard-line, where Columbia had an opportunity to kick a field goal and seal up the victory with 1:43 on the clock.
The elements got in the way again, however, and a dropped snap on the field goal attempt set up Jenny's chance to lead the Big Green, trailing by eight, down the field to tie the game.
That drive never got off the ground, however, and Shalbrack's interception handed Columbia its first win over the Big Green in four years.
"I told them it was a total team win," Columbia head coach Norries Wilson said. "Murphy's Law was probably invented at Columbia because we found a way for something to go wrong at the end, but we also found a way to get past something going wrong at the end."
Dartmouth will host Harvard University at 12:30 p.m. on Saturday at Memorial Field.
