* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
| November |
| | 10 | 7:00PM | Indiana University Southeast | @ | Cumberlands (KY) | 58-80 | |
| | 14 | 8:00PM | Malone College | @ | Cumberlands (KY) | 47-68 | |
| | UC Invitational | |
| | 15 | 4:00PM | Grace College | @ | Cumberlands (KY) | 63-91 | |
| | Championship Game | |
| | 17 | 7:00PM | Johnson University | @ | Cumberlands (KY) | 29-111 | |
| | 20 | 7:00PM | Mountain State University | @ | Cumberlands (KY) | 73-89 | |
| | 28 | 6:00PM | Cumberlands (KY) | vs. | Point Park College | 84-60 | |
| | Ohio Dominican Classic | |
| | 29 | | Cumberlands (KY) | @ | Ohio Dominican College | 84-73 | |
| | Ohio Dominican Classic | |
| December |
| | 2 | 5:00PM | Brescia University | @ | Cumberlands (KY) | 55-76 | |
| | 6 | 4:00PM | Cumberlands (KY) | @ | Indiana University Southeast | 80-49 | |
| | 9 | 7:00PM | Temple Baptist College | @ | Cumberlands (KY) | 52-95 | |
| | 13 | | Cumberlands (KY) | @ | Bellarmine University | 59-77 | |
| | NCAA D-II #21 | |
| | 20 | 7:00PM | Cumberlands (KY) | @ | Marshall University | 70-80 | |
| | NCAA Division I | |
| January |
| | 3 | 3:00PM | World Harvest Bible College | @ | Cumberlands (KY) | 71-88 | |
| | 6 | 7:00PM | Cumberlands (KY) | @ | Mountain State University | 70-85 |  |
| | #1 Mountain State vs #2 Cumberlands | |
| | 8 | 7:00PM | Cumberlands (KY) | @ | Cincinnati-Clermont | 86-65 | |
| * | 15 | 8:00PM | Cumberlands (KY) | @ | Georgetown | 65-74 | |
| * | 17 | 4:00PM | St. Catharine | @ | Cumberlands (KY) | 46-77 | |
| | 19 | 7:00PM | Cumberlands (KY) | @ | Johnson University | 119-55 | |
| * | 22 | 8:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | 69-71 | (OT) |
| * | 24 | 4:00PM | Lindsey Wilson | @ | Cumberlands (KY) | 59-69 | |
| * | 29 | 8:00PM | Cumberlands (KY) | @ | Campbellsville | 71-69 | |
| | 31 | 7:00PM | Cincinnati-Clermont | @ | Cumberlands (KY) | 43-84 | |
| February |
| * | 5 | 8:00PM | Pikeville | @ | Cumberlands (KY) | 58-74 | |
| * | 7 | 4:00PM | Cumberlands (KY) | @ | St. Catharine | 80-45 | |
| * | 12 | 8:00PM | Georgetown | @ | Cumberlands (KY) | 56-53 | |
| * | 14 | 5:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 74-69 | |
| | Lindsey Live | |
| * | 19 | 8:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 79-82 | |
| | 21 | 6:00PM | Cumberlands (KY) | @ | Brescia University | 93-76 | |
| * | 26 | 8:00PM | Campbellsville | @ | Cumberlands (KY) | 57-74 | |
| * | 28 | 4:00PM | Cumberlands (KY) | @ | Pikeville | 79-71 | |
| March |
| | 7 | 6:00PM | Lindsey Wilson | vs. | Cumberlands (KY) | 56-75 | |
| | MSC Tournament Semifinals -- Frankfort, Ky. | |
| | 8 | 3:30PM | Cumberlands (KY) | vs. | Georgetown | 60-57 | |
| | Mid-South Conference Tournament Championship | |
| | 19 | 10:00AM | Cumberlands (KY) | vs. | Jarvis Christian College | 81-65 | |
| | Opening Round of 2009 Buffalo Funds-NAIA Division I Men's Basketball National Championship | |
| | 20 | 5:30PM | Cumberlands (KY) | vs. | Westminster College of Salt Lake City | 62-67 | |
| | 2009 Buffalo Funds-NAIA Division I Men's Basketball National Championship - Sweet 16 | |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (ET)
