| Cumberlands Games/Schedule |
| Regular Season |
| Oct. 25, 2018 | Day 11 | Cumberlands (21) - Milligan | 63-58  |
| Oct. 30, 2018 | Day 16 | Cumberlands (21) - IU Southeast | 78-82  |
| Nov. 2, 2018 | Day 19 | Cumberlands (21) - Bryan | 75-60 |
| Nov. 5, 2018 | Day 22 | Cumberlands (21) - Lindenwood-Bellev. | 84-49 |
| Nov. 9, 2018 | Day 26 | Cumberlands (21) - Faulkner | 63-71 |
| Nov. 10, 2018 | Day 27 | Dalton St. - Cumberlands (21) | 80-82 |
| Nov. 16, 2018 | Day 33 | Cumberlands (21) - Piedmont Internat. | 75-54 |
| Nov. 23, 2018 | Day 39 | Cumberlands (21) - Allen | 90-81 |
| Nov. 24, 2018 | Day 40 | Berkeley, NJ - Cumberlands (21) | 62-59 |
| Nov. 27, 2018 | Day 43 | Cumberlands (21) - Simmons Coll. | 99-55 |
| Dec. 1, 2018 | Day 47 | Carver Bible - Cumberlands (21) | 64-82 |
| Dec. 8, 2018 | Day 54 | IU Southeast - Cumberlands (21) | 84-94 |
| Dec. 15, 2018 | Day 61 | Cumberlands (21) - Johnson, TN | 92-66 |
| Dec. 29, 2018 | Day 71 | Cumberlands (21) - Freed-Hardeman | 80-67 |
| Dec. 30, 2018 | Day 72 | Cumberlands (21) - Xavier, LA | 77-62 |
| Jan. 5, 2019 | Day 78 | Life - Cumberlands (21) | 74-68 |
| Jan. 10, 2019 | Day 83 | Shawnee St. - Cumberlands (21) | 83-74 |
| Jan. 12, 2019 | Day 85 | Pikeville (13) - Cumberlands (21) | 64-63 |
| Jan. 17, 2019 | Day 90 | Cumberlands (21) - Georgetown, KY (1) | 76-62 |
| Jan. 19, 2019 | Day 92 | Cumberlands (21) - Campbellsville | 77-76 |
| Jan. 24, 2019 | Day 97 | Lindsey Wilson - Cumberlands (21) | 66-77 |
| Jan. 26, 2019 | Day 99 | Cumberlands (21) - Cumberland | 59-58 |
| Jan. 31, 2019 | Day 104 | Cumberlands (21) - Pikeville (13) | 52-66 |
| Feb. 2, 2019 | Day 106 | Cumberlands (21) - Shawnee St. | 78-71 |
| Feb. 9, 2019 | Day 112 | Georgetown, KY (1) - Cumberlands (21) | 80-79 |
| Feb. 11, 2019 | Day 114 | Campbellsville - Cumberlands (21) | 64-65 |
| Feb. 14, 2019 | Day 117 | Cumberlands (21) - Life | 75-82 |
| Feb. 16, 2019 | Day 119 | Cumberlands (21) - Carver Bible | 79-51 |
| Feb. 21, 2019 | Day 123 | Cumberlands (21) - Lindsey Wilson | 79-71 |
| Feb. 23, 2019 | Day 125 | Cumberland - Cumberlands (21) | 88-86 |
| Mar. 2, 2019 | Day 129 | Cumberlands (21) - Campbellsville | 87-88 |
| National Tournament Day 1 |
| Mar. 21, 2019 | Day 138 | Wiley (12) - Cumberlands (21) | 68-56 |
