| Cumberlands Games/Schedule |
| Regular Season |
| Oct. 30, 2023 | Day 14 | Camp-Harrodsburg - Cumberlands (7) | 75-116  |
| Nov. 1, 2023 | Day 16 | Ohio Christian - Cumberlands (7) | 65-83 |
| Nov. 3, 2023 | Day 18 | IU Southeast - Cumberlands (7) | 72-76 |
| Nov. 4, 2023 | Day 19 | Midway - Cumberlands (7) | 66-77 |
| Nov. 10, 2023 | Day 25 | Va.Lynchburg - Cumberlands (7) | 64-105 |
| Nov. 11, 2023 | Day 26 | UT Southern - Cumberlands (7) | 65-73 |
| Nov. 14, 2023 | Day 29 | Midway - Cumberlands (7) | 71-93 |
| Nov. 21, 2023 | Day 36 | Dalton St. - Cumberlands (7) | 74-91 |
| Nov. 25, 2023 | Day 39 | Cumberlands (7) - IU East | 83-76 |
| Nov. 26, 2023 | Day 40 | WVU Tech - Cumberlands (7) | 62-79 |
| Nov. 28, 2023 | Day 42 | Cumberlands (7) - St.Mary of the Woods | 93-87 |
| Dec. 9, 2023 | Day 52 | Cumberlands (7) - Rio Grande | 73-60 |
| Dec. 16, 2023 | Day 59 | Cumberlands (7) - IU Southeast | 95-100  |
| Dec. 30, 2023 | Day 69 | Cumberlands (7) - Bryan | 93-85 |
| Jan. 4, 2024 | Day 73 | Johnson, TN - Cumberlands (7) | 64-86 |
| Jan. 11, 2024 | Day 80 | Campbellsville - Cumberlands (7) | 86-91 |
| Jan. 13, 2024 | Day 82 | Georgetown, KY (15) - Cumberlands (7) | 86-94 |
| Jan. 18, 2024 | Day 86 | Cumberland - Cumberlands (7) | 77-100 |
| Jan. 25, 2024 | Day 92 | Cumberlands (7) - Bethel, TN | 95-67 |
| Jan. 27, 2024 | Day 94 | Cumberlands (7) - FHU (5) | 73-81 |
| Feb. 1, 2024 | Day 99 | Cumberlands (7) - Lindsey Wilson | 93-82 |
| Feb. 8, 2024 | Day 105 | Cumberlands (7) - Campbellsville | 104-69 |
| Feb. 10, 2024 | Day 107 | FHU (5) - Cumberlands (7) | 84-91 |
| Feb. 15, 2024 | Day 112 | Lindsey Wilson - Cumberlands (7) | 75-85 |
| Feb. 17, 2024 | Day 114 | Cumberlands (7) - Georgetown, KY (15) | 58-90 |
| Feb. 22, 2024 | Day 118 | Cumberlands (7) - Cumberland | 88-74 |
| Feb. 24, 2024 | Day 120 | Bethel, TN - Cumberlands (7) | 54-83 |
| Conference Quarter-Finals |
| Mar. 2, 2024 | Day 1 | Cumberland - Cumberlands (7) | 81-100 |
| Conference Semi-Finals |
| Mar. 3, 2024 | Day 1 | Georgetown, KY (15) - Cumberlands (7) | 84-81 |
| National Tournament Day 1 |
| Mar. 15, 2024 | Day 125 | Philander Smith - Cumberlands (7) | 96-97 |
| 1/8 Finals |
| Mar. 22, 2024 | Day 127 | Morningside - Cumberlands (7) | 80-74 |
| National Tournament Day 2 |
| Mar. 16, 2024 | Day 126 | Florida Coll. (18) - Cumberlands (7) | 69-80 |
