* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
| November |
| | 1 | 2:00PM | Cumberlands (KY) | @ | Trevecca Nazarene University | 65-78 | |
| | 7 | 6:00PM | Brescia University | @ | Cumberlands (KY) | 45-94 | |
| | High 5 Classic | |
| | 8 | 4:00PM | King College | @ | Cumberlands (KY) | 36-70 | |
| | High 5 Classic | |
| | 14 | 8:00PM | Cumberlands (KY) | vs. | Covenant College | 68-46 | |
| | Gattis Classic at Pikeville | |
| | 15 | 4:00PM | Cumberlands (KY) | vs. | Bluefield College | 65-44 | |
| | Pikeville Classic | |
| | 18 | 5:30PM | Cumberlands (KY) | @ | Southern Polytechnic State University | 60-70 | |
| | 28 | 7:00PM | Cumberlands (KY) | vs. | Cumberland (TN) | 59-44 | |
| | Nationwide Classic | |
| | 29 | 5:00PM | Cumberlands (KY) | vs. | Freed-Hardeman | 76-68 | |
| | Nationwide Classic | |
| December |
| | 5 | 2:00PM | Cumberlands (KY) | vs. | Westminster College of Salt Lake City | 68-51 | |
| | Jim Reid Classic @ Georgetown | |
| | 6 | 2:00PM | Cumberlands (KY) | vs. | St. Francis | 82-73 | |
| | Jim Reid Classic @ Georgetown | |
| | 11 | 6:00PM | Walsh University | @ | Cumberlands (KY) | 63-75 | |
| | 13 | 2:00PM | Ohio Dominican College | @ | Cumberlands (KY) | 65-81 | |
| | 20 | 3:00PM | Cumberlands (KY) | @ | Brescia University | 72-60 | |
| | 28 | 2:00PM | Cumberlands (KY) | @ | West Virginia State | 62-57 | |
| | 29 | 2:00PM | Cumberlands (KY) | @ | University of Charleston | 68-67 | |
| January |
| | 9 | 6:00PM | Cumberlands (KY) | @ | Morris College | 82-63 | |
| | 10 | 4:00PM | Cumberlands (KY) | @ | Allen University | 71-44 | |
| * | 15 | 6:00PM | Cumberlands (KY) | @ | Georgetown | 60-59 | |
| * | 17 | 2:00PM | St. Catharine | @ | Cumberlands (KY) | 49-79 | |
| * | 22 | 6:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | 89-36 | |
| * | 24 | 2:00PM | Lindsey Wilson | @ | Cumberlands (KY) | 64-79 | |
| * | 29 | 6:00PM | Cumberlands (KY) | @ | Campbellsville | 71-79 | (OT) |
| February |
| * | 5 | 6:00PM | Pikeville | @ | Cumberlands (KY) | 60-87 | |
| * | 7 | 2:00PM | Cumberlands (KY) | @ | St. Catharine | 73-57 | |
| * | 12 | 6:00PM | Georgetown | @ | Cumberlands (KY) | 61-79 | |
| * | 14 | 3:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 70-79 | |
| | Lindsey Live | |
| * | 19 | 6:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 54-88 | |
| * | 26 | 6:00PM | Campbellsville | @ | Cumberlands (KY) | 64-70 | |
| * | 28 | 2:00PM | Cumberlands (KY) | @ | Pikeville | 72-53 | |
| March |
| | 7 | 1:00PM | Lindsey Wilson | vs. | Cumberlands (KY) | 51-61 | |
| | MSC Tournament Semifinals -- Frankfort, Ky. | |
| | 8 | 1:00PM | Campbellsville | vs. | Cumberlands (KY) | 57-69 | |
| | Finals of 2009 Mid-South Conference Basketball Tournament-Frankfort Civic Center | |
| | 19 | 5:30PM | Cumberlands (KY) | vs. | Lewis-Clark State College | 76-54 | |
| | Opening Round of the 2009 NAIA Division I Women's Basketball National Tournament in Jackson, TN | |
| | 20 | 9:00PM | Cumberlands (KY) | @ | Freed-Hardeman | 105-99 | (2OT) |
| | Sweet 16 of the 2009 NAIA Division I Women's Basketball National Tournament in Jackson, TN | |
| | 21 | 9:00PM | Lambuth University | vs. | Cumberlands (KY) | 66-54 | |
| | Elite Eight NAIA Division I Women's National Tournament | |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
