* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
| November |
| | 1 | 7:30PM | Asbury College | @ | Cumberlands (KY) | 36-78 | |
| | 2 | 5:30PM | Shorter | @ | Cumberlands (KY) | 67-64 | |
| | 6 | 3:00PM | Cumberlands (KY) | @ | Freed-Hardeman | 77-85 | |
| | 9 | 5:30PM | Allen University | @ | Cumberlands (KY) | 36-81 | |
| | 13 | 3:00PM | Cumberlands (KY) | @ | Union University | 54-81 | |
| | 16 | 6:00PM | Bryan College | @ | Cumberlands (KY) | 40-74 | |
| | 19 | 2:00PM | Cumberlands (KY) | vs. | Davenport University | 70-86 | |
| | Jim Reid Classic - Georgetown, KY | |
| | 20 | 2:00PM | Cumberlands (KY) | vs. | St. Francis | 94-76 | |
| | Jim Reid Classic - Georgetown, KY | |
| | 24 | 2:00PM | Lee University | @ | Cumberlands (KY) | 54-51 | |
| December |
| * | 2 | 6:00PM | Cumberlands (KY) | @ | Pikeville | 62-55 | |
| * | 4 | 2:00PM | Cumberlands (KY) | @ | UVA-Wise | 77-59 | |
| | Listen Live | |
| * | 9 | 7:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 57-45 | |
| | 17 | 1:00PM | Southern Polytechnic State University | @ | Cumberlands (KY) | 56-66 | |
| | 30 | 6:00PM | Cumberlands (KY) | vs. | Trevecca Nazarene University | 48-50 | |
| | Rosa Stokes Classic Cumberland, TN | |
| | 31 | 3:00PM | Cumberlands (KY) | vs. | Cumberland (TN) | 56-53 | |
| | Rosa Stokes Classic Cumberland, TN | |
| January |
| * | 6 | 6:00PM | Rio Grande | @ | Cumberlands (KY) | 66-71 | |
| * | 8 | 2:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 55-82 | |
| * | 13 | 6:00PM | Cumberlands (KY) | @ | Georgetown | 70-64 | |
| * | 15 | 2:00PM | Cumberlands (KY) | @ | Shawnee State | 62-75 | |
| * | 20 | 6:00PM | St. Catharine | @ | Cumberlands (KY) | 47-70 | |
| * | 22 | 2:00PM | Campbellsville | @ | Cumberlands (KY) | 73-60 | |
| | Live Video | |
| * | 27 | 6:00PM | Pikeville | @ | Cumberlands (KY) | 77-75 | (OT) |
| * | 29 | 2:00PM | UVA-Wise | @ | Cumberlands (KY) | 76-74 | |
| February |
| * | 5 | 2:00PM | Lindsey Wilson | @ | Cumberlands (KY) | 72-73 | |
| | Lindsey Live: Stats -- RaiderVision -- Notes | |
| * | 10 | 6:00PM | Cumberlands (KY) | @ | Rio Grande | 82-86 | (OT) |
| * | 12 | 2:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | 75-49 | |
| * | 17 | 6:00PM | Georgetown | @ | Cumberlands (KY) | 79-71 | |
| * | 19 | 2:00PM | Shawnee State | @ | Cumberlands (KY) | 67-45 | |
| * | 24 | 6:00PM | Cumberlands (KY) | @ | St. Catharine | 80-67 | |
| * | 26 | 2:00PM | Cumberlands (KY) | @ | Campbellsville | 72-101 | |
| | Live Video | |
| March |
| | 3 | 2:00PM | Cumberlands (KY) | vs. | Rio Grande | 61-74 | |
| | MSC Tournament Brackets | |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
