Wilmington began its season at Mount St. Joseph University for two games against Heartland Collegiate Athletic Conference (HCAC) foes on Nov. 8-9.
The Quakers fell to Transylvania University, an eventual NCAA Division III Tournament team, 87-78 in the opener, but rebounded to top MSJ at the Harrington Center.
Wilmington blitzed Earlham from the start, scoring the game's first nine points.
That lead would grow to 25-10 midway through the first half.
Earlham cut the deficit to a basket, but it was Wilmington who took a 41-35 lead into halftime.
Earlham took its first lead four minutes into the second half, but Wilmington battled back to take a 72-65 advantage with two minutes to play.
A flurry of triples as well as a couple of missed free throws led to Earlham having the ball down 79-76 in the final minute.
The visitors converted yet another triple while being fouled on the shot. The free throw fell through, and Earlham left Hermann Court with what felt like, to the hosts, a stolen victory.
Wilmington hosted Heidelberg, and the Quakers' recent bad fortune at the end of games finally swung the other direction.
Heidelberg led for the majority of the first half, including by double digits at points, but Wilmington battled back to make the second half a nip-and-tuck affair.
The Quakers found themselves trailing 68-61 after a Student Prince triple with 3:08 to play. Staring at a potential fifth consecutive loss, Wilmington put together a 10-1 run to end the game capped by a game-winning basket from Jeffery Mansfield.
Wilmington then traveled to the University of Mount Union and fell 84-74 in a hard-fought contest. The Quakers then headed north to Michigan to face Olivet College in the final game of the 2019 calendar year. The Quakers overcame a 10-point halftime deficit to escape the Cutler Center with a victory.
The Quakers opened the New Year with consecutive home contests against Marietta College and Capital University. Wilmington fell short in two close contests.
Jeffery Mansfield, who led all scorers in the team's meeting in Berea, got off to a hot start giving WC a 40-25 lead at halftime.
In the second half, the Quakers kept up perhaps their best defensive performance of the season to date.
Abdul Kanu led the way with 24 points and Wilmington won comfortably, 85-70.
Against Muskingum, Dempsey scored a dozen points in the opening stages, but was held to eight the rest of the way.
Muskingum led for over 34 minutes of the game and looked to get a season split up 70-64 with four minutes to go.
Wilmington had other ideas, however, ending the game on a 15-4 run to claim a 79-74 victory and the season sweep.
Riding a three-game winning streak, the Quakers ran into a buzz saw in the form of Ban Johnson Arena. Thanks to 61 first-half points, the Pioneers led nearly the entire way to a 105-74 win.
Two more losses followed - at Capital and at home against John Carroll - to close the season.
Wilmington still qualified for the OAC Tournament, but had to travel back to Marietta, where it had lost just 10 days earlier.
This time around, however, things went very differently. Marietta jumped out to a seven-point lead early, but Wilmington battled back within a single basket in the final minute of the first half.
Unfortunately for the visitors, a banked triple from Marietta gave the Pioneers a six-point (44-38) halftime lead.