The Trojans controlled the tempo against the explosive Jackets' attack, slowing down a team that pushed both Corbin and Cumberland to overtime.
"We knew we couldn't run up and down the floor and play their style. They have too many offensive weapons," Cawood coach Anthony Nolan said. "We wanted to dictate the tempo, and I think we did."
Cawood also got a huge game from junior center Josh Caldwell, who scored 23 points and pulled down 19 rebounds.
"He's still a junior, but he has that veteran experience," Nolan said. "I think he's as hard to guard as any post player in the region and is doing much better about making passes and finding the open man."
Middlesboro coach Bill Jones has been a Caldwell fan for the past couple of years and wasn't surprised at his big game as the Jackets had no answers for him in the post.
"Josh is a hoss, and he hit some big shots," Jones said. "Cawood is getting better. It's always a good game, and coach Nolan does a great job with them."
Cawood showed plenty of patience early but couldn't get shots to fall as Middlesboro built a 13-7 lead while the Trojans missed 10 of 13 shots from the field.
Trailing by nine midway through the second quarter, the Trojans' offense got untracked by turning up the intensity on the defensive end. Senior forward Brad Howard sparked the uprising with two straight steals that led to layups for Caldwell and T.J. Green.
Baskets by Tim McCoun and Dillon Cain and a free throw by Adam Rhymer capped a 9-1 run that pulled the Trojans even at 28-28 at halftime
Sophomore forward Brandon McCoun, who finished with 12 points, had two 3-pointers in a 15-2 run to open the third quarter. Rhymer's three-point play pushed the lead to 43-30 with 2:13 left in the third quarter.
Middlesboro battled back to within five, at 48-43, by the end of the third quarter and pulled even at 50-50 on a 3-pointer by Daniel Griffin with 6:04 left.
After struggling against the Middlesboro pressure, Cawood regrouped and regained the lead for good on a basket by Caldwell with 2:35 to play.
"They put a lot of pressure on, and we got on our heels a little bit instead of continuing to attack," Nolan said. "We started rushing a little, but that will come with experience and maturity over the course of the year."
Middlesboro closed to within one on a three-point play by Nick Smith with 1:08 left but didn't score again as Cawood put the game away on the line, with Green hitting four straight.
"We had some plays called at the end, but we got away from what we were wanting to do," Jones said. "We didn't execute at the end, and Cawood did a good job."
Rhymer and Green added 13 and 11 points, respectively, for the Trojans.
The victory improved Cawood's record to 2-3 overall and 1-0 in the district, ending a three-game losing streak.
"We've got a lot of young people in key spots, and we knew we would go through some growing pains, and we still will," Nolan said.
Smith scored 17 to lead the Jackets, who fell to 2-3 overall and 0-2 in district play.
Both teams return to district action Friday as Cawood plays host to Bell County and Middlesboro is at home against Harlan.
Antwan Brown 2-5 3-4 8, Blaine Green 3-11 0-0 6, Nick Smith 7-12 1-1 17, Chad Cowan 1-2 0-0 2, Will Harrison 2-6 3-4 7, Daniel Griffin 3-13 1-1 9, Eddie Gilbert 2-2 0-0 4, Michael Sulfridge 1-2 2-3 4. Totals: 21-53 10-13 57.
T.J. Green 3-7 4-5 11, Adam Rhymer 3-12 7-9 13, Brandon McCoun 4-9 0-0 12, Brad Howard 0-1 0-0 0, Josh Caldwell 10-17 3-4 23, Dillon Cain 1-3 0-0 2, Mikey Hamlin 0-1 0-0 0, Tim McCoun 1-1 0-0 2, Larry Williamson 0-0 0-0 0. Totals: 22-51 14-18 63.
Middlesboro 13 15 15 14 - 57
Cawood 7 21 20 15 - 63
3-point goals: Middlesboro 5-15 (Smith 2-5, Griffin 2-9, Brown 1-1), Cawood 5-13 (B. McCoun 4-5, Green 1-4, Cain 0-1, Hamlin 0-1, Rhymer 0-2). Rebounds: Middlesboro 22 (Brown, Green 5), Cawood 38 (Caldwell 19). Turnovers: Middlesboro 12, Cawood 19. Fouled out: Middlesboro (Brown).