PHILADELPHIA, Pa. — Sophomore Guilien Smith drove for the tie-breaking layup with 52 seconds left, then made two free throws 30 seconds later before the Dartmouth defense fought off a possible game-tying shot as time expired, giving the Big Green a 76-74 victory over Penn (12-14, 5-8 Ivy) at the Palestra on Friday night. Combined with Brown’s win over Columbia, Dartmouth (7-19, 4-9 Ivy) is still alive in the race for the fourth and final berth in the inaugural Ivy League Tournament.

For the Big Green to earn that berth, they need three outcomes on Saturday night: Dartmouth must hand Princeton its first loss of the season, Harvard has to beat Penn on the road and Yale must hold court at home against Columbia. In that scenario, Dartmouth would be in a three-way tie with the Lions and Quakers, but would win the tiebreaker due to having a better record against the two schools with which it is tied. If Brown also beats Cornell to make it a four-way tie, the Big Green still have the tiebreaker by virtue of its victory over the top seed, Princeton. (CORRECTION: Dartmouth wins the tiebreaker in a four-way tie due to having the best record — 4-2 — against the other three teams in the tie.)

“Sometimes you win these games, sometimes you don’t,” said Dartmouth head coach David McLaughlin after coaching his first game at The Palestra. “In some of those losses, you can rationalize it by knowing you didn’t deserve to win. If we hadn’t pulled this one out, it would have been really hard to shake off because I truly thought we deserved to win as hard and as well as we played.”

Dartmouth ripped off 13 three-pointers on the night in 27 attempts (.481) while shooting 53.7 percent (29-of-54) overall from the floor. That accuracy allowed the Big Green to overcome 18 turnovers while forcing just six, which led to 19 more shots by Penn.

Sophomore Evan Boudreaux led the Big Green offensive charge with 16 points and 12 rebounds for his league-leading 15th double-double of the season, while Smith added 14 with a team-high five assists and junior Miles Wright chipped in 13 thanks to four three-pointers.

Dartmouth led for a majority of the night, building up a double-digit lead in each half, only to have Penn erase them each time. The Big Green enjoyed an early 15-3 run to take an eight-point lead at the outset of the contest, eventually boosting its lead to 11 at 26-15 on a Smith 18-footer above the free throw line. Penn, though, rattled off 13 straight points, seven courtesy of Matt Howard, including the last five to take a 28-26 lead.

Dartmouth maintained its composure, however, reclaiming the lead with 1:37 left in the half on a Wright three-pointer. The Quakers got the last laugh of the opening stanza, however, when Dan Dwyer heaved a long inbounds pass from his own baseline that Howard corralled just inside the arc and fired up as time expired, draining the shot to enter the locker room with the scored deadlocked at 35.

Penn, which entered the game leading the league in defensive field goal percentage, was able to keep pace despite the Big Green shooting 51.7 percent (15-of-29) compared to the Quakers’ 40.5 percent (15-of-37) thanks to 10 Dartmouth turnovers.

In the second half, the Big Green strung together 14 straight points with Boudreaux and senior Mike Fleming each contributing five points to the cause, turning a slim one-point advantage into a 15-point bulge at 54-39 with 13:45 to play.

When Darnell Foreman ended the nearly five-minute Penn scoring drought with a three-pointer, the Quakers were at the outset of an 11-point response with a trio of triples in under two minutes of action.

Junior Taylor Johnson stemmed the tide by driving the baseline for a layup, and Boudreaux added a three-pointer to boost the margin back to eight at 59-51. But Penn took off on a 12-1 spurt, capped by a three-pointer by Howard that gave the hosts a 63-60 lead with under seven minutes to play.

Smith quickly answered with a long ball of his own, somehow banking his three-pointer off the glass from the deep corner opposite the Big Green bench, to knot the score at 63. Wright followed with a rainmaker, as did freshman Brendan Barry after a layup by Penn rookie A.J. Brodeur. A three-point play by Brodeur was negated by another Barry three-ball, leaving Dartmouth up by four, 72-68, with three minutes on the clock.

Foreman, who had 11 points for the Quakers, provided the next two buckets, tying the score for the eighth and final time at 72 with only 1:19 remaining. After a Big Green timeout, Smith — who had just returned to the floor after picking up his fourth foul five minutes earlier — drove down the lane and beat his man to the rim for the go-ahead layup.

Brodeur missed a contested shot in the lane moments later, and Smith dropped two free throws through with 22.3 seconds left. Ryan Betley, who matched Howard with 19 points and three trifectas, quickly scored to keep Penn within two. The Quakers then forced a turnover on the inbounds play, giving them one last chance to tie or take the lead. Foreman tried to get to the rim but was cut off by the defense, instead settling for a turnaround jumper that bounced off the iron, and Wright secured the rebound as time expired to give Dartmouth the hard-fought road win.

Thanks to Boudreaux and Wright (seven rebounds), the Big Green enjoyed a 40-31 advantage on the glass. The defense as a unit held Penn to 42.5 percent shooting (31-of-73) and a mere 26.7 percent (8-of-30) from behind the arc. Neither team attempted more than eight free throws with Dartmouth hitting five and the Quakers four.

The Big Green tip off at Princeton (20-6, 13-0) on Saturday at 6 p.m. The game will be streamed by both the Ivy League Digital Network and ESPN3. Penn’s showdown with Harvard begins at 7 p.m.

Notes: Dartmouth’s 13 three-pointers matched its season high attained just two weeks ago in an 80-79 overtime victory over Columbia ... the Big Green have won three straight games against Penn for the first time since 1958-59 ... Dartmouth also enjoyed just its second series sweep of the Quakers since the 1958-59 season, the other taking place in 2009 ... all four of the Green’s Ivy League victories have come with at least 12 three-pointers made ... this was Dartmouth’s first victory on a Friday this season (1-6).