* Conference Event
% Scrimmage Event
Event times are (ET)
| November |
| | 2 | 6:00PM | Indiana University Northwest | @ | Cumberlands (KY) | 15-93 | |
| | U. of the Cumberlands "High 5" Classic |
| | 3 | 4:00PM | Milligan College | @ | Cumberlands (KY) | 72-78 | |
| | U. of the Cumberlands "High 5" Classic |
| | 9 | 3:00PM | Cumberlands (KY) | vs. | Williams Baptist College | 67-56 | |
| | @ Bethel College Classic |
| | 10 | 5:00PM | Cumberlands (KY) | vs. | Bethel | 66-61 | |
| | @ Bethel College Classic |
| | | 5:00PM | Cumberlands (KY) | @ | Bethel | 66-61 | |
| | McKenzie Rotary Club Classic |
| | 16 | 8:00PM | Cumberlands (KY) | vs. | Shawnee State University | 74-63 | |
| | @ Pikeville College Classic |
| | 17 | 2:00PM | Martin Methodist | vs. | Cumberlands (KY) | 53-65 | |
| | Pikeville College Classic |
| | 24 | 3:30PM | Cumberlands (KY) | @ | Southern Indiana | 72-84 | |
| | 30 | 5:00PM | Cumberlands (KY) | vs. | Hillsdale College | 48-66 | |
| | @ West Virginia U. Tech Classic |
| December |
| | 1 | 5:00PM | Cumberlands (KY) | vs. | Chowan College | 63-41 | |
| | @ West Virginia U. Tech Classic |
| | 15 | 3:00PM | Lee University | @ | Cumberlands (KY) | 87-83 | (OT) |
| | 18 | 9:00PM | Cumberlands (KY) | @ | Azusa Pacific University | 57-68 |  |
| | 30 | | Cumberlands (KY) | @ | Temple Baptist College | 99-17 | |
| | 31 | 3:00PM | Cumberlands (KY) | @ | University of Northwestern Ohio | 79-47 | |
| January |
| | 2 | 3:00PM | Southern Polytechnic State University | @ | Cumberlands (KY) | 56-80 | |
| | 5 | 3:00PM | Cumberlands (KY) | @ | Columbia College | 76-64 | |
| | 7 | 2:00PM | Cumberlands (KY) | @ | College of the Ozarks | 68-73 | |
| | 12 | 2:00PM | Allen University | @ | Cumberlands (KY) | 24-90 | |
| | 19 | 2:00PM | Cumberlands (KY) | @ | Temple Baptist College | 84-26 | |
| | 21 | 6:00PM | Brescia University | @ | Cumberlands (KY) | 61-62 | |
| * | 26 | 2:00PM | Lindsey Wilson | @ | Cumberlands (KY) | 71-68 | |
| | Lindsey Live |
| * | 31 | 6:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | 84-64 | |
| February |
| * | 2 | 2:00PM | Georgetown | @ | Cumberlands (KY) | 54-66 | |
| * | 7 | 6:00PM | Campbellsville | @ | Cumberlands (KY) | 69-94 | |
| * | 9 | 2:00PM | Cumberlands (KY) | @ | Pikeville | 84-47 | |
| | (@ East Ky. Expo Center) |
| * | 16 | 3:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 65-67 | |
| | Lindsey Live -- Audio -- Stats |
| * | 21 | 6:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 48-95 | |
| * | 23 | 2:00PM | Cumberlands (KY) | @ | Georgetown | 93-90 | (2OT) |
| * | 28 | 2:00PM | Cumberlands (KY) | @ | Campbellsville | 87-77 | |
| March |
| * | 1 | 2:00PM | Pikeville | @ | Cumberlands (KY) | 61-90 | |
| | 9 | 3:00PM | Cumberlands (KY) | vs. | Georgetown | 63-66 | |
| | Semi-Finals of MSC Tournament -- Live Stats |
| | 20 | 4:30PM | Cumberlands (KY) | @ | Vanguard University | 62-75 | |
| | First Round of NAIA National Tournament |
* Conference Event
% Scrimmage Event
Event times are (ET)
