A basket by Brandon McCoun and two free throws from Adam Rhymer cut the Trojans' deficit to 48-47 with 6:57 left in the game. The free throws helped Rhymer become the 19th member of the school's 1,000-point club.
Brock Leisge hit a 3-pointer and had a layup and Desmond Johnson had a putback as Cumberland went on a 7-0 run to regain the momentum.
Leisge made three of four free throws and Johnson and Kyle Hogue had two apiece as the Redskins escaped with the victory.
"Cawood came out and had a good game plan," Cumberland coach Jerry Edwards said. "They played hard and played physical and left it all out on the floor. (Cawood coach) Anthony (Nolan) is getting the best out of his team. They'll be a team to be reckon with come district (tournament) time.
"We competed all night," said Nolan. "I thought we played hard. We had three straight possessions to take a lead, and we took some bad shots or some quick shots.
"Hopefully, we'll get a couple of those lucky bounces by tournament time - we've sure not got any all year. Man for man, our kids played hard all night."
Leisge powered the Redskins with 22 points, including a 10-for-12 effort from the free throw line. Johnson scored 18 points, grabbed 17 rebounds and had seven blocked shots.
"I think both teams played hard and left it all out on the floor," said Edwards. "It's nothing to be ashamed of either way.
"Desmond was three block shots short of a triple-double. Brock hit some big shots, and in the first half, Paul David Creech came in the game and hit some big 3s and did whatever he had to do to help us."
The lead changed hands five times in the first quarter. Johnson had two baskets and Garfield Wilson scored three points as the Redskins scored nine in a row and led 21-13 after one period.
T.J. Green hit two free throws and added a basket as the Trojans cut the deficit to 28-26 with 4:43 to play in the second quarter.
Creech nailed a pair of 3-pointers and Wilson and Johnson scored two points each as the Redskins scored 10 straight and led 38-30 at halftime.
Rhymer had two treys and McCoun added another as the Trojans outscored Cumberland 13-9 in the third quarter.
Rhymer, a senior guard, finished the night with 24 points. McCoun contributed 15 points.
"People don't realize, we've got three different people out there on the court playing out of position and have been all season," said Nolan. "These kids are learning their roles and working hard. All we need to do is be aggressive, like we were tonight, and I think good things will happen."
Edwards was pleased with his team's performance.
"We're not going to have one star every night. It's going to be a team effort. It's going to be somebody different every night, and that's how good teams get to the big show," he said.
"Everybody contributes something to the game. I'm proud with the way we played. This is a hard place to win, and we had such a long drought, and we're just proud to get the win."
The Redskins held a 46-19 rebounding advantage.
"They're aggressive," Nolan said of Cumberland. "They work hard to get in position to rebound."
The Redskins improved to 16-3 overall and 9-0 in district competition. They will complete their district schedule when they travel to Bell County on Friday at 7:30 p.m. with a chance to clinch the top seed in the upcoming district tournament.
Cawood (8-16, 4-5) plays host to Harlan on Friday in the second game of the girls/boys doubleheader at 7:30 p.m.
Brock Leisge 5-16 10-12 22, Brooks Hogue 0-5 1-2 1, Blake Polson 1-2 0-0 2, Desmond Johnson 8-12 2-5 18, Garfield Wilson 2-10 2-7 6, Paul David Creech 3-8 0-0 8, Kyle Hogue 0-2 3-4 3, Tyrek Simmons 1-3 0-0 2. Totals: 20-58 18-30 62.
Adam Rhymer 8-20 5-6 24, Dillon Cain 0-4 0-0 0, Tim McCoun 1-5 0-0 2, Brad Howard 0-1 1-5 1, Brandon McCoun 6-9 1-2 15, T.J. Green 1-2 2-4 4, Josh Lemar 2-3 1-1 5, Aaron Watkins 0-1 2-2 2, Mikey Hamlin 0-0 0-0 0. Totals: 18-45 12-20 53.
Cumberland 21 17 9 15 - 62
Cawood 13 17 13 10 - 53
3-point goals: Cumberland 4-21 (Creech 2-7, Leisge 2-8, Johnson 0-1, K. Hogue 0-2, B. Hogue 0-3), Cawood 5-13 (Rhymer 3-5, B. McCoun 2-4, Cain 0-1, Watkins 0-1, T. McCoun 0-2). Rebounds: Cumberland 46 (Johnson 17), Cawood 19 (Howard 5). Assists: Cumberland 8 (Leisge 4), Cawood 9 (T. McCoun, Howard 3). Turnovers: Cumberland 13, Cawood 14. Fouled out: Cawood (Green).