Turnovers also stung UMBC in its comeback effort, as the Retrievers committed 13 of 20 miscues in the second half.
Fry and UMBC got off to a solid start, as the grad student hit his first six shots from the floor in a 12-point first half. His fast break layup at the 12:50 mark of the first half gave the visitors a 12-6 lead, but Penn responded with a 9-2 run and took a 15-14 lead on a Jack Eggleston trey at the 9:10 mark.
Forward Laurence Jolicoeur (Queens, N.Y./Holy Cross/Manhattan) hit a three-pointer with 3:13 to play in the half and knot the score at 23-all, but the Quakers went on a 9-3 run to close the half and lead, 32-26, at intermission.
The Quakers would build the lead to as many as 15 points at 52-37 midway through the second half, but Retriever guard Travis King (New Haven, Conn./New Hyde Leadership/George Washington) sparked an 8-1 UMBC flurry with a pair of treys and the Retrievers were within, 53-45, with nine minutes remaining.
Penn would not make a field goal in the final twelve minutes of play, but converted 22 of 28 free throws in the final 8:34 to keep UMBC out of striking distance.
Fry finished 8-of-14 from the field and led UMBC with seven rebounds. King, held to two first-half points, hit 4-of-7 from behind the arc in the final 20 minutes and finished with 14 points. Jolicoeur added 13 points, while guard Chris De La Rosa (Washington Heights, N.Y./All Hallows/Siena) scored nine points and added a game-high eight assists.
UMBC hit all 12 of its free throw attempts and is 26 of 28 in its last two games.
But Penn became the fourth team in six games to hit 50 percent or better from the floor against UMBC, converting on 19 of 36 (52.8 percent) attempts. UMBC hit 20 of 48 shots (41.7 percent) and was outrebounded, 24-22.
The Retrievers travel to Hartford to take on ninth-ranked U. Conn on Friday.