* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
| September |
| * | 5 | 2:00PM | Rio Grande | @ | Cumberlands (KY) | 1-3 | |
| | 8 | 5:00PM | Milligan College | @ | Cumberlands (KY) | 1-2 | (OT) |
| | 12 | 2:00PM | Cumberlands (KY) | @ | Mount Vernon Nazarene College | 0-1 | (OT) |
| | 16 | 2:00PM | Cumberlands (KY) | @ | Union | 1-2 | (OT) |
| | Listen Live | |
| * | 19 | 2:00PM | Cumberlands (KY) | @ | Pikeville | 6-0 | |
| * | 22 | 3:00PM | Georgetown | @ | Cumberlands (KY) | 1-3 | |
| | 26 | 4:00PM | Montreat College | @ | Cumberlands (KY) | RAIN | |
| | 29 | 4:00PM | Lincoln Memorial University | @ | Cumberlands (KY) | 3-0 | |
| October |
| | 3 | 5:00PM | Cincinnati Christian University | @ | Cumberlands (KY) | 1-2 | |
| * | 7 | 6:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 0-6 | |
| | Lindsey Live | |
| | 10 | 2:00PM | Cumberlands (KY) | @ | Asbury College | 1-7 | |
| * | 13 | 4:00PM | Campbellsville | @ | Cumberlands (KY) | 3-5 | |
| | 20 | 7:00PM | Cumberlands (KY) | @ | Bryan College | 1-0 | (OT) |
| * | 24 | 3:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 1-1 | (2OT) |
| | 28 | 1:30PM | Oakland City University | @ | Cumberlands (KY) | 0-6 | |
| | 31 | 2:00PM | Cumberlands (KY) | @ | Tennessee Wesleyan | 4-3 | |
| November |
| * | 2 | 3:00PM | Cumberlands (KY) | @ | St. Catharine | 4-1 | |
| | 6 | 1:00PM | Pikeville | @ | Cumberlands (KY) | 1-4 | |
| | Mid-South Conference Tournament First Round | |
| | 12 | | Cumberlands (KY) | @ | Georgetown | 2-2 | (2OT) |
| | Mid-South Conference Tournament Semifinals - Georgetown advances 8-7 on penalty kicks. | |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
