* Conference Event
% Scrimmage Event
Event times are (ET)
| November |
| % | 3 | | Cumberlands (KY) | @ | Mississippi State | 60-71 | |
| | Exhibition |
| | 6 | 7:00PM | Cumberlands (KY) | @ | Mountain State University | 62-79 |  |
| | 9 | 6:00PM | Cumberlands (KY) | vs. | Milligan College | 73-80 | |
| | @ King College Tournament |
| | 10 | 4:00PM | Cumberlands (KY) | @ | King College | 91-72 | |
| | @ King College Tournament |
| | 16 | 8:00PM | Purdue University Calumet | @ | Cumberlands (KY) | 59-85 | |
| | UCIT Tournament |
| | 17 | 4:00PM | Shorter | @ | Cumberlands (KY) | 70-69 | (OT) |
| | U. of the Cumberlands Tournament |
| | 20 | 7:30PM | Cumberlands (KY) | @ | Berea College | 79-73 | |
| | 23 | 6:00PM | Cumberlands (KY) | vs. | Miami-Middletown | 90-48 | |
| | @ Ohio Dominican Tournament |
| | 24 | | Cumberlands (KY) | vs. | Ohio Dominican College | 66-65 | |
| | @ Ohio Dominican Tournament |
| | 30 | 5:00PM | Trevecca Nazarene University | vs. | Cumberlands (KY) | 77-73 | |
| | TNU Audio -
Cumberland (Tenn.) Classic - Lebanon, Tenn. |
| December |
| | 1 | 7:00PM | Cumberlands (KY) | @ | Cumberland (TN) | 62-69 | |
| | Rosa Stokes Classic |
| | 4 | 7:30PM | Cumberlands (KY) | @ | Tennessee Temple | 83-64 | |
| | 8 | 3:00PM | Cumberlands (KY) | vs. | Asbury College | 64-68 | |
| | 15 | 2:00PM | King College | @ | Cumberlands (KY) | 76-82 | (OT) |
| | 31 | 7:00PM | Cumberlands (KY) | @ | Bellarmine University | 69-94 | |
| January |
| | 5 | 3:00PM | Tennessee Wesleyan | @ | Cumberlands (KY) | 47-81 | |
| | 12 | 4:00PM | Mountain State University | @ | Cumberlands (KY) | 97-90 | |
| | 15 | 7:30PM | Tennessee Temple | @ | Cumberlands (KY) | 55-100 | |
| | 17 | 7:30PM | Cincinnati-Clermont | @ | Cumberlands (KY) | 71-93 | |
| | 24 | 7:30PM | Cumberlands (KY) | @ | Brescia University | 73-52 | |
| * | 26 | 4:00PM | Lindsey Wilson | @ | Cumberlands (KY) | 46-49 | |
| | Lindsey Live |
| * | 31 | 8:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | 59-58 | |
| February |
| * | 2 | 4:00PM | Georgetown | @ | Cumberlands (KY) | 77-70 | |
| * | 7 | 8:00PM | Campbellsville | @ | Cumberlands (KY) | 63-46 | |
| * | 9 | 4:00PM | Cumberlands (KY) | @ | Pikeville | 78-66 | |
| | 14 | 6:00PM | Brescia University | @ | Cumberlands (KY) | 60-63 | |
| * | 16 | 5:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 73-56 | |
| | Lindsey Live -- Audio -- Stats |
| * | 21 | 8:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 61-88 | |
| * | 23 | 4:00PM | Cumberlands (KY) | @ | Georgetown | 68-80 | |
| * | 28 | 8:00PM | Cumberlands (KY) | @ | Campbellsville | 76-74 | (OT) |
| March |
| * | 1 | 4:00PM | Pikeville | @ | Cumberlands (KY) | 78-64 | |
| | 9 | 6:00PM | Campbellsville | vs. | Cumberlands (KY) | 63-73 | |
| | MSC Tournament Semi-Finals @ East KY Expo Center, Pikeville ,KY |
| | 10 | 1:30PM | Georgetown | vs. | Cumberlands (KY) | 73-59 | |
| | MSC Tournament at Eastern Ky. Expo Center -- Live Stats |
| | 20 | 7:15PM | Cumberlands (KY) | @ | Lewis-Clark State College | 75-62 | |
| | First Round NAIA National Tournament |
| | 21 | 9:00PM | Cumberlands (KY) | vs. | Lee University | 72-84 | |
| | Sweet Sixteen of NAIA Tournament |
* Conference Event
% Scrimmage Event
Event times are (ET)
