* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
| November |
| | 1 | 2:00PM | Cumberlands (KY) | @ | Trevecca Nazarene University | 65-78 | |
| | 7 | 6:00PM | Brescia University | @ | Cumberlands (KY) | 45-94 | |
| | High 5 Classic |
| | 8 | 4:00PM | King College | @ | Cumberlands (KY) | 36-70 | |
| | High 5 Classic |
| | 14 | 8:00PM | Cumberlands (KY) | vs. | Covenant College | 68-46 | |
| | Gattis Classic at Pikeville |
| | 15 | 4:00PM | Cumberlands (KY) | vs. | Bluefield College | 65-44 | |
| | Pikeville Classic |
| | 18 | 5:30PM | Cumberlands (KY) | @ | Southern Polytechnic State University | 60-70 | |
| | 28 | 7:00PM | Cumberlands (KY) | vs. | Cumberland (TN) | 59-44 | |
| | Nationwide Classic |
| | 29 | 5:00PM | Cumberlands (KY) | vs. | Freed-Hardeman | 76-68 | |
| | Nationwide Classic |
| December |
| | 5 | 2:00PM | Cumberlands (KY) | vs. | St. Francis | | |
| | Jim Reid Classic @ Georgetown |
| | 6 | 2:00PM | Cumberlands (KY) | vs. | Westminster College of Salt Lake City | | |
| | Jim Reid Classic @ Georgetown |
| | 11 | 6:00PM | Walsh University | @ | Cumberlands (KY) | | |
| | 13 | 2:00PM | Ohio Dominican College | @ | Cumberlands (KY) | | |
| | 20 | 3:00PM | Cumberlands (KY) | @ | Brescia University | | |
| | 28 | 2:00PM | Cumberlands (KY) | @ | West Virginia State | | |
| | 29 | 2:00PM | Cumberlands (KY) | @ | University of Charleston | | |
| January |
| | 9 | 6:00PM | Cumberlands (KY) | @ | Morris College | | |
| | 10 | 4:00PM | Cumberlands (KY) | @ | Allen University | | |
| * | 15 | 6:00PM | Cumberlands (KY) | @ | Georgetown | | |
| * | 17 | 2:00PM | St. Catharine | @ | Cumberlands (KY) | | |
| * | 22 | 6:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | | |
| * | 24 | 2:00PM | Lindsey Wilson | @ | Cumberlands (KY) | | |
| * | 29 | 6:00PM | Cumberlands (KY) | @ | Campbellsville | | |
| February |
| * | 5 | 6:00PM | Pikeville | @ | Cumberlands (KY) | | |
| * | 7 | 2:00PM | Cumberlands (KY) | @ | St. Catharine | | |
| * | 12 | 6:00PM | Georgetown | @ | Cumberlands (KY) | | |
| * | 14 | 3:00PM | Cumberlands (KY) | @ | Lindsey Wilson | | |
| * | 19 | 6:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | | |
| * | 26 | 6:00PM | Campbellsville | @ | Cumberlands (KY) | | |
| * | 28 | 2:00PM | Cumberlands (KY) | @ | Pikeville | | |
| March |
| | 5 | | Cumberlands (KY) | vs. | Conference Tourney | | |
| | MSC Conference @ Frankfort, KY |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
