| October |
| | 30 | 7:00PM | Central Christian | @ | Union College | 97-61 | |
| | | 8:00PM | Rocky Mountain College | vs. | Haskell | 88-77 | |
| | MSU-Northern Tournament |
| | 31 | 6:00PM | Haskell | @ | Montana State University-Northern | 64-82 | |
| | | 7:00PM | Jamestown College | @ | Peru | 67-63 | |
| | | 7:30PM | Dakota Wesleyan University | @ | York | 72-53 |  |
| | Cornerstone Classic |
| November |
| | 1 | | Concordia University | @ | York | 74-57 | |
| | | 3:15PM | Viterbo University | @ | College of the Ozarks | 57-68 | |
| | Homecoming |
| | | 5:00PM | Valley City State University | @ | Peru | 72-58 | |
| | | 7:00PM | Nebraska Christian College | @ | Bellevue | 49-104 | |
| | 3 | 7:30PM | Central Bible College | @ | Oklahoma Wesleyan | 51-77 | |
| | 4 | 7:00PM | Bethany College | @ | Haskell | 67-69 | |
| | | 7:00PM | Vennard College | @ | Central Christian | 53-80 | |
| | | 7:00PM | College of the Ozarks | @ | Lyon College | 83-63 | |
| | | 7:30PM | Dordt College | @ | Bellevue | 50-76 | |
| | | 7:30PM | Peru | @ | Hastings College | 68-89 | |
| | | 7:30PM | York | @ | Briar Cliff University | 66-109 | |
| | | 8:30PM | Friends University | @ | Oklahoma Wesleyan | 76-83 | |
| | 7 | | Bethel College | vs. | Haskell | 71-83 | |
| | McPherson Classic |
| | | 6:00PM | Bellevue | vs. | William Woods University | 91-59 | |
| | Mount Mercy Tournament - Nov. 7-8 (Cedar Rapids, IA) |
| | | 7:30PM | Oklahoma Wesleyan | vs. | Evangel University | 82-77 | |
| | Evangel Classic - Sadiel Rojas scored 23 pts and 14 rebs in only 23 minutes |
| | | 8:30PM | Briar Cliff University | @ | Peru | 90-68 | |
| | Peru State Classic |
| | 8 | | McPherson College | vs. | Haskell | 84-72 | |
| | McPherson Classic |
| | | 3:00PM | Central Christian | @ | Calvary Bible College | 101-35 | |
| | | 4:00PM | Bellevue | vs. | Mount Mercy College | 79-63 | |
| | Mount Mercy Tournament - Nov. 7-8 (Cedar Rapids, IA) |
| | | 4:00PM | College of the Ozarks | @ | Graceland University | 81-73 | |
| | Jared Howerton scored 24 points and grabbed 11 rebounds |
| | | 4:00PM | Oklahoma Wesleyan | @ | Central Bible College | 77-47 | |
| | Evangel Classic |
| | | 7:00PM | Doane College | @ | Peru | 75-70 | |
| | | 7:30PM | York | @ | Midland Lutheran College | 68-72 | |
| | 10 | 8:00PM | Haskell | @ | Tabor College | 91-97 | |
| | 11 | 7:00PM | Northwestern College | @ | Bellevue | 92-88 | |
| | | 7:00PM | College of the Ozarks | @ | Evangel University | 64-79 | |
| | | 7:30PM | SCU | @ | Central Christian | 91-83 | |
| | | 7:30PM | Doane College | @ | York | 84-59 | |
| | | 8:00PM | Peru | @ | Dana College | 58-83 | |
| | 12 | 8:00PM | Haskell | @ | Ottawa University | 78-103 | |
| | 13 | 7:30PM | SCU | @ | Oklahoma Wesleyan | 96-109 | |
| | 14 | 5:00PM | Cedarville University | vs. | College of the Ozarks | 67-50 | |
| | Shawnee State Classic; Portsmouth, OH |
| | | 6:00PM | Johnson & Wales University | @ | Central Christian | 83-70 | |
| | | 7:00PM | Southern Nazarene University | @ | Haskell | 76-74 | |
| | | 7:30PM | Peru | @ | Tabor College | 56-93 | |
| | 15 | 3:00PM | College of the Ozarks | @ | Shawnee State University | 82-62 | |
| | Shawnee State Classic |
| | | 4:00PM | Midland Lutheran College | @ | Bellevue | 60-79 | |
| % | | 7:00PM | Central Christian | @ | Fort Hays State University | 65-86 | |
| | | 7:00PM | Peru | @ | Sterling College | 55-76 | |
| | | 7:30PM | Haskell | @ | Bethany College | 83-76 | |
| | 18 | 7:00PM | York | @ | Friends University | 38-79 | |
| | | 7:30PM | Bellevue | @ | Benedictine College | 70-58 | |
| | | 7:30PM | Manhattan Christian College | @ | Central Christian | 67-65 | |
| | | 7:30PM | William Woods University | @ | College of the Ozarks | 60-62 | |
| | | 8:00PM | Oklahoma Wesleyan | @ | Southwestern College | 95-70 | |
| | Steve Briggs - 37 points, Sadiel Rojas - double-double (17 points 11 rebs) |
| | 19 | 7:00PM | Haskell | @ | Kansas Wesleyan University | 72-70 | |
| | 21 | 4:00PM | Oklahoma Wesleyan | vs. | Bethel College | 78-73 | |
| | Friends Classic |
| | | 6:00PM | Morningside College | vs. | Bellevue | 75-77 | |
| | MLC Draemel Classic |
| | | 7:00PM | Dakota State University | @ | Peru | 83-67 | |
| | | 7:00PM | York | @ | Concordia University | 59-88 | |
| | | 8:00PM | College of the Ozarks | @ | Sterling College | 57-63 | |
| | Sterling Classic |
| | 22 | 4:00PM | Bellevue | @ | Midland Lutheran College | 92-66 | |
| | MLC Draemel Classic |
| | | 4:00PM | Bacone College | @ | Haskell | 67-92 | |
| | | 4:00PM | College of the Ozarks | vs. | Tabor College | 65-52 | |
| | Sterling Classic |
| | | 6:00PM | Oklahoma Wesleyan | @ | Friends University | 61-57 | |
| | Friends Classic |
| | 24 | 7:00PM | Tabor College | @ | Haskell | 77-71 | |
| | | 7:30PM | Oklahoma Wesleyan | @ | SCU | 104-107 | (OT) |
| | | 8:00PM | McPherson College | @ | Central Christian | 98-96 | (2OT) |
| | 25 | 7:00PM | Peru | @ | Avila College | 69-78 | |
| | 26 | 7:00PM | York | @ | University of Nebraska-Kearney | 48-84 | |
| | 28 | 3:00PM | Haskell | @ | South Dakota School of Mines & Tech. | 86-97 | |
| | SD Mines Classic |
| | | 5:00PM | Peru | @ | Black Hills State University | 55-71 | |
| | 29 | | Bellevue | vs. | Westmont College | 79-73 | (OT) |
| | Trips Sports Classic - Nov. 29-30 (San Antonio, TX) |
| | | 3:00PM | Haskell | vs. | Black Hills State University | 63-81 | |
| | SD Mines Classic |
| | | 5:00PM | Peru | @ | South Dakota School of Mines & Tech. | 74-96 | |
| | 30 | | Bellevue | vs. | Rodgers State | 79-85 | |
| | Trips Sports Classic - Nov. 28-29 (San Antonio, TX) |
| December |
| | 1 | 7:00PM | Ottawa University | @ | Haskell | 95-90 | |
| | | 7:30PM | McPherson College | @ | Oklahoma Wesleyan | 81-98 | |
| | 2 | 7:30PM | Central Christian | @ | Manhattan Christian College | 63-71 | |
| | | 7:30PM | Nebraska Christian College | @ | Peru | 63-82 | |
| | 4 | 7:00PM | Robert Morris College | @ | College of the Ozarks | 72-74 | |
| | Cam Jam Classic |
| | | 7:30PM | Oklahoma Wesleyan | @ | Bacone College | 97-83 | |
| | 5 | 7:30PM | Dallas Christian College | @ | Central Christian | 66-73 | |
| | 6 | 1:00PM | Missouri Baptist College | @ | College of the Ozarks | 68-70 | |
| | McDonald's Cam Jam Classic |
| | | 3:00PM | Calvary Bible College | @ | Central Christian | 47-91 | |
| | | 5:00PM | Baptist Bible College | @ | Oklahoma Wesleyan | 73-101 | |
| | | 6:00PM | York | @ | University of Sioux Falls | 59-89 | |
| | 9 | 7:30PM | York | @ | University of Nebraska-Omaha | 58-101 | |
| | 10 | 7:00PM | William Penn College | @ | Bellevue | 79-85 | |
| % | | 7:00PM | Central Christian | @ | Emporia State University | 51-107 | |
| | 11 | 7:00PM | Lyon College | @ | College of the Ozarks | 58-85 | |
| | 13 | 3:00PM | Ozark Christian College | @ | Central Christian | 52-78 | |
| | | 4:00PM | York | @ | Newman University | 68-119 | |
| | | 6:00PM | Peru | @ | Dakota State University | 78-86 | |
| | 16 | 8:30PM | Oklahoma Wesleyan | @ | Southwestern Assemblies of God Univ | 100-68 | |
| | Southwestern Assemblies of God Classic |
| | 17 | 7:30PM | Oklahoma Wesleyan | vs. | Mount Vernon Nazarene College | 85-81 | |
| | Southwestern Assemblies of God Classic - OWU No. 4, MVNU No. 24 |
| | 20 | | College of the Ozarks | vs. | University of the Sacred Heart | 76-59 | |
| | San Juan, Puerto Rico Classic |
| | | 4:00PM | Bellevue | @ | Hastings College | 74-73 | |
| | | 7:00PM | York | @ | Wayne State College | 62-94 | |
| | 21 | | College of the Ozarks | vs. | University of Wisconsin-Stout | 64-70 | (2OT) |
| | San Juan, Puerto Rico Classic |
| | 29 | 7:00PM | Haskell | @ | Southern Nazarene University | 48-97 | |
| | 30 | 6:00PM | Bellevue | vs. | Dordt College | 75-65 | |
| | Pizza Ranch Classic |
| | | 8:00PM | York | @ | Northwestern College | 50-92 | |
| | Pizza Ranch Classic |
| | 31 | 6:00PM | Dordt College | vs. | York | 104-73 | |
| | Pizza Ranch Classic |
| | | 8:00PM | Bellevue | @ | Northwestern College | 87-78 | |
| | Pizza Ranch Classic |
| January |
| | 3 | 3:00PM | Ozark Christian College | @ | Oklahoma Wesleyan | 44-106 | |
| | | 5:00PM | Peru | @ | Johnson & Wales University | 68-80 | |
| | 5 | 7:30PM | McPherson College | @ | York | 82-69 | |
| | 7 | 7:00PM | Bellevue | @ | Park University | 65-66 | |
| | | 7:30PM | York | @ | Grace University | 73-72 | |
| | 8 | 8:00PM | Dana College | @ | Peru | 89-60 | |
| | 9 | 7:30PM | Central Christian | @ | SCU | 71-87 | |
| | 10 | 5:00PM | Central Christian | @ | Hillsdale Free Will Baptist College | 114-110 | (OT) |
| | | 5:00PM | Park University | @ | College of the Ozarks | 77-87 | (OT) |
| | 12 | 8:00PM | Friends University | @ | Central Christian | 88-95 | (OT) |
| * | 13 | 7:30PM | Bellevue | @ | Peru | 83-52 | |
| | | 7:30PM | Oklahoma Wesleyan | @ | Ecclesia College | 69-64 | |
| | 14 | 7:00PM | Haskell | @ | Bacone College | 89-83 | (OT) |
| * | 16 | 7:30PM | Oklahoma Wesleyan | @ | Haskell | 99-65 | |
| * | | 7:30PM | College of the Ozarks | @ | Central Christian | 92-83 | |
| * | | 7:30PM | Peru | @ | York | 56-63 | |
| * | 17 | 5:00PM | Bellevue | @ | York | 114-75 | |
| * | | 5:00PM | Oklahoma Wesleyan | @ | Central Christian | 92-72 | |
| * | | 5:00PM | College of the Ozarks | @ | Haskell | 78-70 | |
| | 20 | 7:00PM | Park University | @ | Peru | 79-59 | |
| * | | 7:30PM | Oklahoma Wesleyan | @ | College of the Ozarks | 76-87 | |
| * | 23 | 7:30PM | Central Christian | @ | Bellevue | 56-93 | |
| * | | 7:30PM | York | @ | College of the Ozarks | 60-108 | |
| * | | 7:30PM | Haskell | @ | Peru | 78-67 | |
| * | 24 | 5:00PM | Haskell | @ | Bellevue | 63-95 | |
| * | | 5:00PM | York | @ | Oklahoma Wesleyan | 53-104 | |
| * | | 5:00PM | Central Christian | @ | Peru | 54-51 | |
| | 26 | 8:00PM | Union College | @ | Central Christian | 41-91 | |
| * | 27 | 7:30PM | Haskell | @ | Central Christian | 84-81 | (OT) |
| | | 7:30PM | Evangel University | @ | College of the Ozarks | PPD | |
| * | 30 | 7:30AM | Peru | @ | College of the Ozarks | 62-84 | |
| * | | 7:00PM | Bellevue | @ | Oklahoma Wesleyan | 88-95 | (OT) |
| * | | 7:30PM | Central Christian | @ | York | 83-72 | |
| * | 31 | 5:00PM | Bellevue | @ | College of the Ozarks | 76-83 | |
| * | | 5:00PM | Peru | @ | Oklahoma Wesleyan | 45-79 | |
| * | | 5:00PM | Haskell | @ | York | 93-65 | |
| February |
| * | 3 | 7:30PM | Central Christian | @ | Haskell | 71-75 | |
| | | 7:30PM | College of the Ozarks | @ | Park University | 57-64 | |
| * | 6 | 7:30PM | Oklahoma Wesleyan | @ | Bellevue | 86-74 | |
| * | | 7:30PM | York | @ | Central Christian | 85-111 | |
| * | | 7:30PM | College of the Ozarks | @ | Peru | 70-41 | |
| * | 7 | 5:00PM | College of the Ozarks | @ | Bellevue | 64-72 | |
| * | | 5:00PM | Oklahoma Wesleyan | @ | Peru | 92-76 | |
| * | | 5:00PM | York | @ | Haskell | 74-103 | |
| | 9 | 7:00PM | Peru | @ | Park University | 63-86 | |
| * | 10 | 7:30PM | College of the Ozarks | @ | Oklahoma Wesleyan | 64-80 | |
| | | 7:30PM | Hillsdale Free Will Baptist College | @ | Central Christian | 74-105 | |
| | 12 | 7:30PM | Bacone College | @ | Oklahoma Wesleyan | 48-83 | |
| * | 13 | 7:30PM | Bellevue | @ | Central Christian | 81-62 | |
| * | | 7:30PM | Peru | @ | Haskell | 52-80 | |
| * | | 7:30PM | College of the Ozarks | @ | York | 99-65 | |
| * | 14 | 5:00PM | Bellevue | @ | Haskell | 86-93 | |
| * | | 5:00PM | Oklahoma Wesleyan | @ | York | 93-69 | |
| * | | 5:00PM | Peru | @ | Central Christian | 62-74 | |
| * | 17 | 7:00PM | Peru | @ | Bellevue | 57-85 | |
| | | 7:30PM | Ecclesia College | @ | Oklahoma Wesleyan | 69-107 | |
| | 20 | 7:00PM | Park University | @ | Bellevue | 61-83 | |
| * | | 7:30PM | Haskell | @ | Oklahoma Wesleyan | 70-89 | |
| | Wesleyan clinches 2008-09 MCAC regular season championship |
| * | | 7:30PM | Central Christian | @ | College of the Ozarks | 73-70 | |
| * | | 7:30PM | York | @ | Peru | 87-86 | |
| * | 21 | 5:00PM | York | @ | Bellevue | 73-109 | |
| * | | 5:00PM | Central Christian | @ | Oklahoma Wesleyan | 84-101 | |
| * | | 5:00PM | Haskell | @ | College of the Ozarks | 69-65 | |
| | 27 | 5:30PM | College of the Ozarks | vs. | Bellevue | 72-54 | |
| | MCAC Tournament Semifinals (Bartlesville, Okla.) |
| | | 7:30PM | Haskell | @ | Oklahoma Wesleyan | 80-102 | |
| | MCAC Tournament Semifinals (Bartlesville, Okla.) |
| | 28 | 5:00PM | College of the Ozarks | @ | Oklahoma Wesleyan | 63-84 | |
| | MCAC Tournament Final (Bartlesville, Okla.) |
| March |
| | 2 | 7:00PM | Evangel University | @ | College of the Ozarks | 74-82 | |
| | 11 | 4:00PM | Bellevue | vs. | Mount Vernon Nazarene College | 84-75 | |
| | NAIA National Tournament (Point Lookout, Mo.) |
| | | 8:00PM | Aquinas College | @ | College of the Ozarks | 60-71 | |
| | NAIA Division II Tournament - First Round |
| | 12 | 7:30PM | Oklahoma Wesleyan | vs. | Fisher College | 115-74 | |
| | NAIA Div. II National Tournament Round 1 |
| | | 8:00PM | Ecclesia College | @ | Central Christian | 86-81 | |
| | NCCAA Central Regional Tournament |
| | 13 | 10:15AM | Bellevue | vs. | Oregon Institute of Technology | 78-64 | |
| | NAIA National Tourament (Point Lookout, Mo.) |
| | | 7:30PM | University of Sioux Falls | @ | College of the Ozarks | 56-70 | |
| | NAIA National Tournament - Second Round - Keeter Gymnasium in Point Lookout, Missouri |
| | | 9:15PM | Oklahoma Wesleyan | vs. | Grand View University | 74-68 | |
| | NAIA Div. II National Tournament 'Sweet 16' |
| | 14 | 1:00PM | Bellevue | vs. | Bethel College | 77-82 | |
| | NAIA National Tournament (Point Lookout, Mo.) |
| | | 6:00PM | Indiana Wesleyan University | @ | College of the Ozarks | 70-79 | |
| | NAIA Division II National Tournament - semifinals |
| | 15 | 8:00PM | Oklahoma Wesleyan | vs. | Eastern Oregon University | 80-79 | |
| | NAIA Div. II National Tournament 'Elite Eight' |
| | 16 | | Bethel College | @ | College of the Ozarks | 64-73 | |
| | NAIA Division II National Semifinals (Point Lookout, Mo.) |
| | | | Oklahoma Wesleyan | vs. | Black Hills State University | 85-72 | |
| | NAIA Division II National Semifinals (Point Lookout, Mo.) |
| | 17 | 8:45PM | Oklahoma Wesleyan | @ | College of the Ozarks | 60-53 | |
| | NAIA Division II National Championship Game (Point Lookout, Mo.) |
