Robbie Jackson and Chris De La Rosa had career games against the former Northeast Conference foe, but UMBC missed three late shots to drop the hard fought battle, 89-86.
Jackson led the way with 24 points off eight field goals and eight free throws with 15 rebounds, all of which marked career highs for the Marshall transfer.
Fellow transfer De La Rosa scored a game high 25 points off 11 field goals while grabbing seven rebounds, all of which marked career highs.
Chauncey Gilliam and Shawn Grant each recorded 12 points in the contest. For Grant it ended a two game scoring drought, and marked his first double-digit outing since he scored 12 points against Toledo earlier this month.
But while UMBC had four players come up big, the Blue Devils had five as Robby Ptacek, Vince Rosario, David Simmons, Shemik Thompson, and Joe Seymore all scored at least 12 points. Ptacek led the team with 23 points as all but Thompson surpassed their season averages.
UMBC had a great shot to end the game at the end of the first overtime when De La Rosa went up for a game-winning shot with one second left, but he made an inexperienced move and opted to pass to a wide open man on the wing as time expired.
They had a few chances in the second overtime but missed three straight shots while they were forced to foul Central Connecticut State players in hopes of conserving the clock.
Despite the hard fought battle, UMBC has now fallen to 1-11 and will begin conference play on January 2 against the 9-5 Vermont Catamounts. Vermont was picked to finish second in the pre-season coaches polls and is home to two-time Player and Defensive Player of the Year Marqus Blakely. He has been assisted by former Michigan State guard Maurice Joseph, who is in his second season as a Catamount.