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* Conference Event
% Exhibition/Scrimmage Event
Event times are (EST)
| November |
| | 3 | 7:30PM | Central Bible College | @ | Oklahoma Wesleyan | 51-77 | |
| | 4 | 8:30PM | Friends University | @ | Oklahoma Wesleyan | 76-83 | |
| | 7 | 7:30PM | Oklahoma Wesleyan | vs. | Evangel University | 82-77 | |
| | Evangel Classic - Sadiel Rojas scored 23 pts and 14 rebs in only 23 minutes | |
| | 8 | 4:00PM | Oklahoma Wesleyan | @ | Central Bible College | 77-47 | |
| | Evangel Classic | |
| | 13 | 7:30PM | Southwestern Christian | @ | Oklahoma Wesleyan | 96-109 | |
| | 18 | 8:00PM | Oklahoma Wesleyan | @ | Southwestern College | 95-70 | |
| | Steve Briggs - 37 points, Sadiel Rojas - double-double (17 points 11 rebs) | |
| | 21 | 4:00PM | Oklahoma Wesleyan | vs. | Bethel College | 78-73 | |
| | Friends Classic | |
| | 22 | 6:00PM | Oklahoma Wesleyan | @ | Friends University | 61-57 | |
| | Friends Classic | |
| | 24 | 7:30PM | Oklahoma Wesleyan | @ | Southwestern Christian | 104-107 | (OT) |
| December |
| | 1 | 7:30PM | McPherson College | @ | Oklahoma Wesleyan | 81-98 | |
| | 4 | 7:30PM | Oklahoma Wesleyan | @ | Bacone College | 97-83 | |
| | 6 | 5:00PM | Baptist Bible College | @ | Oklahoma Wesleyan | 73-101 | |
| | 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 | |
| January |
| | 3 | 3:00PM | Ozark Christian College | @ | Oklahoma Wesleyan | 44-106 | |
| | 13 | 7:30PM | Oklahoma Wesleyan | @ | Ecclesia College | 69-64 | |
| * | 16 | 7:30PM | Oklahoma Wesleyan | @ | Haskell | 99-65 | |
| * | 17 | 5:00PM | Oklahoma Wesleyan | @ | Central Christian | 92-72 | |
| * | 20 | 7:30PM | Oklahoma Wesleyan | @ | College of the Ozarks | 76-87 | |
| * | 24 | 5:00PM | York | @ | Oklahoma Wesleyan | 53-104 | |
| * | 30 | 7:00PM | Bellevue | @ | Oklahoma Wesleyan | 88-95 | (OT) |
| * | 31 | 5:00PM | Peru State College | @ | Oklahoma Wesleyan | 45-79 | |
| February |
| * | 6 | 7:30PM | Oklahoma Wesleyan | @ | Bellevue | 86-74 | |
| * | 7 | 5:00PM | Oklahoma Wesleyan | @ | Peru State College | 92-76 | |
| * | 10 | 7:30PM | College of the Ozarks | @ | Oklahoma Wesleyan | 64-80 | |
| | 12 | 7:30PM | Bacone College | @ | Oklahoma Wesleyan | 48-83 | |
| * | 14 | 5:00PM | Oklahoma Wesleyan | @ | York | 93-69 | |
| | 17 | 7:30PM | Ecclesia College | @ | Oklahoma Wesleyan | 69-107 | |
| * | 20 | 7:30PM | Haskell | @ | Oklahoma Wesleyan | 70-89 | |
| | Wesleyan clinches 2008-09 MCAC regular season championship | |
| * | 21 | 5:00PM | Central Christian | @ | Oklahoma Wesleyan | 84-101 | |
| | 27 | 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 |
| | 12 | 7:30PM | Oklahoma Wesleyan | vs. | Fisher College | 115-74 | |
| | NAIA Div. II National Tournament Round 1 | |
| | 13 | 9:15PM | Oklahoma Wesleyan | vs. | Grand View University | 74-68 | |
| | NAIA Div. II National Tournament 'Sweet 16' | |
| | 15 | 8:00PM | Oklahoma Wesleyan | vs. | Eastern Oregon University | 80-79 | |
| | NAIA Div. II National Tournament 'Elite Eight' | |
| | 16 | | 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.) | |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (EST)
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