| October |
| | 26 | 2:00PM | Ohio State University-Mansfield | @ | Georgetown | 32-133 | |
| % | 30 | 8:00PM | Georgetown | vs. | Kentucky Wesleyan University | 72-85 | |
| November |
| % | 1 | 1:30PM | Georgetown | @ | University of Louisville | 67-74 | |
| | University of Louisville ranked #3 in ESPN/USA Today Preseason Poll | |
| | | 7:00PM | Glenville State College | @ | West Virginia U. Tech | 72-62 | |
| | | 8:00PM | Lambuth University | @ | St. Catharine | 85-77 | |
| | 2 | 2:00PM | Maryland Bible | @ | West Virginia U. Tech | 66-75 | |
| % | 3 | 8:00PM | Campbellsville | @ | University of Arkansas-Fayetteville | | |
| | 5 | | Cumberland (TN) | @ | St. Catharine | 78-67 | |
| | | 7:00PM | Ohio State-Marion | @ | West Virginia U. Tech | 33-102 | |
| | | 7:30PM | Georgetown | @ | Virginia Intermont College | 91-79 | |
| | 7 | 5:00PM | St. Catharine | vs. | Martin Methodist | 59-79 | |
| | at Bethel College | |
| | | 8:00PM | Free Will Baptist Bible College | @ | Pikeville | 50-118 | |
| | BB&T Classic | |
| | | 9:00PM | Mid-Continent College | @ | Lindsey Wilson | 85-82 | (2OT) |
| | Lindsey Wilson Classic | |
| | 8 | 1:00PM | Mid-Continent College | vs. | Campbellsville | 74-78 | |
| | Lindsey Wilson College Classic in Columbia, KY | |
| | | 2:00PM | University of Northwestern Ohio | @ | Georgetown | 66-76 | |
| | | 5:00PM | Bluefield College | @ | Lindsey Wilson | 77-79 | |
| | Lindsey Wilson Classic | |
| | | 7:00PM | St. Catharine | @ | Bethel | 68-79 | |
| | Live Stats | |
| | | 7:30PM | West Virginia U. Tech | @ | Shawnee State | 68-70 | |
| | | 8:00PM | UVA-Wise | @ | Pikeville | 63-72 | |
| | BB&T Classic | |
| | 10 | 7:00PM | Indiana University Southeast | @ | Cumberlands (KY) | 58-80 | |
| | | 7:00PM | Pikeville | @ | Shawnee State | 65-60 | |
| | | 7:30PM | West Virginia U. Tech | @ | Virginia Intermont College | 90-78 | |
| | 11 | 8:00PM | Tennessee Temple | @ | Lindsey Wilson | 44-71 | |
| | Listen Live | |
| % | | 9:30PM | Georgetown | @ | Brigham Young University | 57-80 | |
| | 12 | 7:00PM | Southern Virginia University | @ | West Virginia U. Tech | 75-83 | |
| | 13 | 7:00PM | Boyce College | @ | Lindsey Wilson | 37-90 | |
| | 14 | 5:00PM | Pikeville | vs. | Union University | 79-85 | |
| | McKendree Classic | |
| | | 7:00PM | Auburn University Montgomery | vs. | Campbellsville | 83-73 | (2OT) |
| | Faulkner Classic in Montgomery, AL Campbellsville ranked 18th; AUM ranked 21st | |
| | | 8:00PM | Malone College | @ | Cumberlands (KY) | 47-68 | |
| | UC Invitational | |
| | 15 | 4:00PM | Grace College | @ | Cumberlands (KY) | 63-91 | |
| | Championship Game | |
| | | 5:00PM | Pikeville | vs. | Indiana University-South Bend | 84-71 | |
| | McKendree Classic | |
| | | 6:00PM | Johnson University | @ | Lindsey Wilson | 27-122 | |
| | Lindsey Live -- Stats -- Audio | |
| | | 7:00PM | Campbellsville | @ | Faulkner | 57-59 | |
| | Faulkner Classic in Montgomery, AL | |
| % | 16 | 2:00PM | West Virginia U. Tech | @ | Marshall University | 57-110 | |
| | 17 | 7:00PM | Johnson University | @ | Cumberlands (KY) | 29-111 | |
| | | 7:30PM | Ohio Dominican College | @ | Georgetown | 82-80 | |
| | | 8:00PM | St. Catharine | @ | Lambuth University | 61-84 | |
| % | 18 | 8:00PM | Campbellsville | @ | Western Kentucky | 48-62 | |
| | exhibition at WKU | |
| | 19 | 7:00PM | St. Catharine | @ | Alice Lloyd College | 76-80 | (OT) |
| | 20 | 7:00PM | Mountain State University | @ | Cumberlands (KY) | 73-89 | |
| | | 7:30PM | Asbury College | @ | Georgetown | 60-74 | |
| % | | 8:00PM | Campbellsville | @ | Samford University | 54-73 | |
| | exhibition in Birmingham, AL | |
| | 22 | 2:00PM | Evangel University | @ | Campbellsville | 78-74 | |
| | | 2:00PM | Southern Polytechnic State University | @ | Georgetown | 68-84 | |
| | | 3:00PM | Roanoke Bible | @ | West Virginia U. Tech | 43-112 | |
| | | 4:00PM | Lindsey Wilson | @ | Purdue University Calumet | 65-43 | |
| | | 4:00PM | Indiana University Southeast | @ | Pikeville | 80-74 | |
| | | 7:00PM | St. Catharine | @ | Berea College | 71-81 | |
| | 24 | 7:00PM | St. Catharine | @ | University of Northwestern Ohio | 69-79 | |
| | 25 | 7:00PM | St. Catharine | @ | Wright State-Lake | 77-86 | |
| | | 7:30PM | Boyce College | @ | Georgetown | 31-111 | |
| | | 8:00PM | Freed-Hardeman | @ | Lindsey Wilson | 60-73 | |
| | Lindsey Live: Audio -- Stats | |
| | | 8:00PM | Pikeville | @ | Alice Lloyd College | 88-76 | |
| | 28 | 3:00PM | St. Catharine | vs. | Asbury College | 60-72 | |
| | Spalding University Thanksgiving Classic - Louisville | |
| | | 6:00PM | Cumberlands (KY) | vs. | Point Park College | 84-60 | |
| | Ohio Dominican Classic | |
| | | 6:00PM | Pikeville | vs. | Bluefield College | 90-103 | |
| | Bluefield State Classic | |
| | | 7:00PM | Lindsey Wilson | vs. | Taylor University | 44-41 | |
| | Lou Cunningham Classic -- Lindsey Live | |
| | | 8:00PM | Virginia Intermont College | @ | Campbellsville | 48-79 | |
| | Lou Cunningham Classic at Campbellsville | |
| | 29 | | Cumberlands (KY) | @ | Ohio Dominican College | 84-73 | |
| | Ohio Dominican Classic | |
| | | 3:00PM | Lindsey Wilson | vs. | Virginia Intermont College | 78-66 | |
| | Lou Cunningham Classic -- Lindsey Live | |
| | | 4:00PM | Taylor University | @ | Campbellsville | 64-66 | |
| | Lou Cunningham Classic at Campbellsville | |
| | | 4:00PM | Apprentice School | @ | West Virginia U. Tech | 103-107 | |
| | | 6:00PM | Pikeville | @ | Bluefield State College | 88-79 | |
| | Bluefield State Classic | |
| % | | 8:00PM | St. Catharine | @ | Murray State University | 66-76 | |
| | 30 | 6:00PM | St. Catharine | @ | Spalding University | 56-55 | |
| | Spalding University Thanksgiving Classic - Louisville | |
| December |
| | 1 | 7:30PM | Spalding University | @ | Campbellsville | 50-64 | |
| | 2 | 5:00PM | Brescia University | @ | Cumberlands (KY) | 55-76 | |
| | | 7:00PM | West Virginia U. Tech | @ | Southern Virginia University | 71-88 | |
| | 3 | 7:30PM | Spalding University | @ | Georgetown | 49-89 | |
| | 4 | 8:00PM | Alice Lloyd College | @ | Pikeville | 84-105 | |
| | 5 | 4:00PM | St. Catharine | vs. | Aquinas College | 59-73 | |
| | Georgetown College Tournament December 5-6 | |
| | | 8:00PM | Edward Waters | @ | Georgetown | 70-86 | |
| | Jim Reid Classic | |
| | | 8:00PM | Tennessee Temple | @ | West Virginia U. Tech | 64-86 | |
| | Baisi Classic Tournament | |
| | 6 | | St. Catharine | vs. | Edward Waters | 63-81 | |
| | Georgetown College Tournament Dec 5-6 | |
| % | | 12:00PM | Campbellsville | @ | North Alabama | 70-76 | |
| | exhibition at NCAA DII North Alabama | |
| | | 2:00PM | Davenport University | @ | Lindsey Wilson | 67-76 | |
| | | 4:00PM | Cumberlands (KY) | @ | Indiana University Southeast | 80-49 | |
| | | 4:00PM | Temple Baptist College | @ | Pikeville | 54-102 | |
| | | 8:00PM | Aquinas College | @ | Georgetown | 46-68 | |
| | Jim Reid Classic--Championship Game | |
| | | 8:00PM | Cincinnati-Clermont | @ | West Virginia U. Tech | 62-89 | |
| | Baisi Classic | |
| | 8 | 8:00PM | Urbana University | vs. | Campbellsville | 64-70 | |
| | @ Gallatin County High School (Warsaw, KY) | |
| | 9 | 7:00PM | Temple Baptist College | @ | Cumberlands (KY) | 52-95 | |
| | | 7:00PM | Union University | @ | Georgetown | 62-78 | |
| | 12 | 6:00PM | Union University | vs. | Campbellsville | 86-65 | |
| | Freed-Hardeman Classic in Henderson, TN | |
| | 13 | | Cumberlands (KY) | @ | Bellarmine University | 59-77 | |
| | NCAA D-II #21 | |
| | | 3:00PM | Virginia Intermont College | @ | West Virginia U. Tech | 56-58 | |
| | | 4:00PM | Kentucky Christian | @ | Pikeville | 66-84 | |
| | | 5:00PM | Warren Wilson College | @ | Lindsey Wilson | 52-110 | |
| | Lindsey Live | |
| | | 5:00PM | Campbellsville | @ | Freed-Hardeman | 62-71 | |
| | Freed-Hardeman Classic in Henderson, TN | |
| | 16 | 7:00PM | Lindsey Wilson | @ | Southern Polytechnic State University | 72-56 | |
| | 19 | 7:00PM | Alice Lloyd College | @ | St. Catharine | 68-87 | |
| | | 8:00PM | Ohio State University-Mansfield | @ | Pikeville | 42-116 | |
| | 20 | 3:00PM | Ohio State University-Mansfield | @ | West Virginia U. Tech | 58-111 | |
| | | 7:00PM | Cumberlands (KY) | @ | Marshall University | 70-80 | |
| | NCAA Division I | |
| | 29 | 8:00PM | Wheeling Jesuit University | @ | Pikeville | 93-86 | |
| | Main Street Classic at Wheeling, W.Va. | |
| | 30 | 2:00PM | UVA-Wise | @ | Georgetown | 66-100 | |
| | | 6:00PM | Pikeville | vs. | West Liberty State | 110-114 | (2OT) |
| | Main Street Classic | |
| January |
| | 2 | 2:00PM | Virginia Intermont College | @ | Georgetown | 55-82 | |
| | | 7:30PM | King College | @ | Campbellsville | 78-83 | |
| | 3 | 3:00PM | World Harvest Bible College | @ | Cumberlands (KY) | 71-88 | |
| | | 4:00PM | Lindsey Wilson | @ | Mountain State University | 73-92 | |
| | Lindsey Live | |
| | | 4:00PM | King College | @ | Georgetown | 50-98 | |
| | | 7:30PM | Cumberland (TN) | @ | Campbellsville | 56-50 | |
| | 4 | 3:00PM | Shawnee State | @ | West Virginia U. Tech | 53-83 | |
| | 5 | 2:00PM | Saint Xavier University | @ | Georgetown | 63-85 | |
| | | 7:00PM | The University of Akron Wayne College | @ | West Virginia U. Tech | 53-97 | |
| | | 8:00PM | St. Catharine | @ | Cumberland (TN) | 55-73 | |
| | 6 | 7:00PM | Cumberlands (KY) | @ | Mountain State University | 70-85 |  |
| | #1 Mountain State vs #2 Cumberlands | |
| | 7 | 7:30PM | Campbellsville | @ | Urbana University | 68-71 | |
| | | 8:30PM | Georgetown | @ | University of Saint Francis | 82-51 | |
| | 8 | 7:00PM | Cumberlands (KY) | @ | Cincinnati-Clermont | 86-65 | |
| | | 7:00PM | Berea College | @ | St. Catharine | 62-67 | |
| | 9 | 7:00PM | Temple Baptist College | @ | Campbellsville | 58-79 | |
| | 10 | 4:00PM | Temple Baptist College | @ | Lindsey Wilson | 64-73 | |
| | | 4:00PM | Olivet Nazarene University | @ | Georgetown | 51-64 | |
| | | 4:00PM | West Virginia U. Tech | @ | Rio Grande | 84-97 | |
| | | 4:00PM | Berea College | @ | Pikeville | 77-94 | |
| | 11 | 2:00PM | Ohio State University-Mansfield | @ | Lindsey Wilson | PPD | |
| | 12 | 7:00PM | Temple Baptist College | @ | St. Catharine | 46-87 | |
| | 13 | 8:00PM | Brescia University | @ | Lindsey Wilson | 77-81 | (2OT) |
| | Lindsey Live | |
| * | 15 | 8:00PM | Campbellsville | @ | Pikeville | 62-71 | |
| * | | 8:00PM | Cumberlands (KY) | @ | Georgetown | 65-74 | |
| * | | 8:00PM | West Virginia U. Tech | @ | St. Catharine | 70-64 | |
| * | 17 | 4:00PM | Georgetown | @ | Campbellsville | 85-56 | |
| * | | 4:00PM | St. Catharine | @ | Cumberlands (KY) | 46-77 | |
| | | 4:00PM | West Virginia U. Tech | @ | Mountain State University | 96-91 | |
| * | | 5:00PM | Pikeville | @ | Lindsey Wilson | 67-71 | |
| | Lindsey Live | |
| | 19 | 7:00PM | Cumberlands (KY) | @ | Johnson University | 119-55 | |
| * | 22 | 8:00PM | Lindsey Wilson | @ | Campbellsville | 65-62 | |
| | Lindsey Live | |
| * | | 8:00PM | Cumberlands (KY) | @ | West Virginia U. Tech | 69-71 | (OT) |
| * | | 8:00PM | Pikeville | @ | Georgetown | 58-84 | |
| | 24 | 3:00PM | Brescia University | @ | Campbellsville | 80-74 | |
| * | | 4:00PM | Lindsey Wilson | @ | Cumberlands (KY) | 59-69 | |
| * | | 4:00PM | Georgetown | @ | West Virginia U. Tech | 80-78 | |
| * | | 8:00PM | St. Catharine | @ | Pikeville | 77-88 | |
| | 29 | 7:00PM | Temple Baptist College | @ | Pikeville | 52-102 | |
| * | | 8:00PM | Cumberlands (KY) | @ | Campbellsville | 71-69 | |
| * | | 8:00PM | West Virginia U. Tech | @ | Lindsey Wilson | 63-67 | |
| * | | 8:00PM | Georgetown | @ | St. Catharine | 76-60 | |
| * | 31 | 4:00PM | Campbellsville | @ | St. Catharine | 61-68 | (OT) |
| * | | 4:00PM | West Virginia U. Tech | @ | Pikeville | 66-74 | |
| * | | 5:00PM | Georgetown | @ | Lindsey Wilson | 75-77 | (OT) |
| | OT | |
| | | 7:00PM | Cincinnati-Clermont | @ | Cumberlands (KY) | 43-84 | |
| February |
| * | 5 | 8:00PM | Campbellsville | @ | West Virginia U. Tech | 59-75 | |
| * | | 8:00PM | Lindsey Wilson | @ | St. Catharine | 71-69 | |
| * | | 8:00PM | Pikeville | @ | Cumberlands (KY) | 58-74 | |
| * | 7 | 4:00PM | Lindsey Wilson | @ | Pikeville | 56-66 | |
| * | | 4:00PM | Campbellsville | @ | Georgetown | 45-73 | |
| * | | 4:00PM | Cumberlands (KY) | @ | St. Catharine | 80-45 | |
| | 9 | 7:00PM | Victory University | @ | West Virginia U. Tech | 68-94 | |
| | 10 | 7:00PM | Mountain State University | @ | Lindsey Wilson | 69-83 | |
| | Lindsey Live | |
| * | 12 | 8:00PM | Pikeville | @ | Campbellsville | 77-69 | |
| * | | 8:00PM | Georgetown | @ | Cumberlands (KY) | 56-53 | |
| * | | 8:00PM | St. Catharine | @ | West Virginia U. Tech | 61-67 | |
| * | 14 | 4:00PM | Pikeville | @ | St. Catharine | 85-77 | |
| * | | 4:00PM | West Virginia U. Tech | @ | Georgetown | 52-82 | |
| * | | 5:00PM | Cumberlands (KY) | @ | Lindsey Wilson | 74-69 | |
| | Lindsey Live | |
| | | 7:00PM | Ohio State University-Mansfield | @ | Campbellsville | 51-100 | |
| | 15 | 3:00PM | Ohio State University-Mansfield | @ | Lindsey Wilson | 59-141 | |
| * | 19 | 8:00PM | West Virginia U. Tech | @ | Cumberlands (KY) | 79-82 | |
| * | | 8:00PM | Georgetown | @ | Pikeville | 80-84 | |
| * | | 9:00PM | Campbellsville | @ | Lindsey Wilson | 58-66 | |
| | Lindsey Live | |
| * | 21 | 4:00PM | Lindsey Wilson | @ | Georgetown | 46-79 | |
| * | | 4:00PM | St. Catharine | @ | Campbellsville | 67-70 | |
| * | | 4:00PM | Pikeville | @ | West Virginia U. Tech | 71-86 | |
| | | 6:00PM | Cumberlands (KY) | @ | Brescia University | 93-76 | |
| | 23 | 7:00PM | Ohio State University-Mansfield | @ | Campbellsville | | |
| * | 26 | 7:00PM | Lindsey Wilson | @ | West Virginia U. Tech | 62-66 | |
| | | 7:00PM | Pikeville | @ | Mountain State University | 71-97 | |
| * | | 8:00PM | Campbellsville | @ | Cumberlands (KY) | 57-74 | |
| * | | 8:00PM | St. Catharine | @ | Georgetown | 42-78 | |
| * | 28 | 4:00PM | West Virginia U. Tech | @ | Campbellsville | 63-77 | |
| * | | 4:00PM | Cumberlands (KY) | @ | Pikeville | 79-71 | |
| * | | 6:00PM | St. Catharine | @ | Lindsey Wilson | 63-77 | |
| | Lindsey Live | |
| March |
| | 6 | 6:00PM | Campbellsville | vs. | Lindsey Wilson | 60-64 | (OT) |
| | Opening Round of 2009 Mid-South Conference Basketball Tournament-Frankfort Civic Center-Frankfort, KY | |
| | | 8:00PM | Pikeville | vs. | West Virginia U. Tech | 81-67 | |
| | Mid-South Conference Tournament | |
| | 7 | 6:00PM | Lindsey Wilson | vs. | Cumberlands (KY) | 56-75 | |
| | MSC Tournament Semifinals -- Frankfort, Ky. | |
| | | 8:00PM | Georgetown | vs. | Pikeville | 77-53 | |
| | Mid-South Conference Tournament | |
| | 8 | 3:30PM | Cumberlands (KY) | vs. | Georgetown | 60-57 | |
| | Mid-South Conference Tournament Championship | |
| | 18 | | Georgetown | vs. | Central Methodist College | 64-73 | |
| | NAIA National Tournament (Kansas City, MO) | |
| | 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 | |
| | | 10:45PM | Lindsey Wilson | vs. | Texas Wesleyan University | 69-75 | |
| | NAIA National Championships -- Kansas City, Mo. -- March 18-24 | |
| | 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 | |
