2008-09 Midland Men's Basketball Schedule
- * Conference Event
- %Scrimmage
- ^ Exhibition
- Event times are (CST)
| | Day | Time | Location | | Opponent | Score | | | Record |
| October |
| | 31 | 12:00 PM | | vs. | Valley City State University | L-62-78 | | | 0-1 |
| November |
| | 1 | 3:30 PM | | vs. | Jamestown College | L-53-54 | | | 0-2 |
| | 5 | 7:30 PM | | @ | Grand View University | L-67-81 | | | 0-3 |
| | 8 | 7:30 PM | | vs. | York College | W-72-68 | | | 1-3 |
| | 15 | 4:00 PM | | @ | Bellevue University | L-60-79 | | | 1-4 |
| | 16 | 2:00 PM | | vs. | Iowa Wesleyan College | L-66-70 | | | 1-5 |
| | 21 | 8:00 PM | | vs. | University of St. Mary | W-79-66 | | | 2-5 |
| | MLC Draemel Classic |
| | 22 | 4:00 PM | | vs. | Bellevue University | L-66-92 | | | 2-6 |
| | MLC Draemel Classic |
| * | 25 | 8:00 PM | | vs. | Dana College | W-80-75 | | | 3-6 1-0 |
| December |
| * | 3 | 8:00 PM | | @ | Hastings | L-56-70 | | | 3-7 1-1 |
| * | 6 | 4:00 PM | | vs. | Northwestern | L-74-91 | | | 3-8 1-2 |
| * | 13 | 4:00 PM | | @ | Briar Cliff | L-72-84 | | | 3-9 1-3 |
| * | 16 | 8:00 PM | | @ | Doane | W-67-62 | | | 4-9 2-3 |
| | 17 | 7:30 PM | | vs. | Grand View University | L-57-67 | | | 4-10 |
| | 21 | 3:00 PM | | @ | University of South Dakota | L-64-86 | | | 4-11 |
| | 28 | 2:00 PM | | @ | Northern State University | L-74-77 | | | 4-12 |
| January |
| * | 3 | 4:00 PM | | vs. | Dakota Wesleyan | L-73-84 | | | 4-13 2-4 |
| * | 7 | 8:00 PM | | @ | Morningside | L-56-66 | | | 4-14 2-5 |
| * | 10 | 4:00 PM | | vs. | Mount Marty | W-59-56 | | | 5-14 3-5 |
| * | 14 | 7:30 PM | | vs. | Concordia | L-73-81 | | | 5-15 3-6 |
| * | 17 | 4:00 PM | | @ | Dana College | L-68-81 | | | 5-16 3-7 |
| * | 21 | 8:00 PM | | vs. | Nebraska Wesleyan | W-63-57 | | | 6-16 4-7 |
| * | 24 | 4:00 PM | | vs. | University of Sioux Falls | L-80-87 | | | 6-17 4-8 |
| * | 28 | 8:00 PM | | vs. | Hastings | L-66-91 | | | 6-18 4-9 |
| * | 31 | 4:00 PM | | @ | Dordt | L-51-87 | | | 6-19 4-10 |
| February |
| * | 3 | 7:30 PM | | @ | Concordia | L-53-59 | | | 6-20 4-11 |
| * | 11 | 7:30 PM | | vs. | Doane | L-79-81 | | | 6-21 4-12 |
| | Tyler Weatherholt hit a 12-foot shot for the game winner at the buzzer |
| * | 14 | 4:00 PM | | @ | Mount Marty | W-67-65 (OT) | | | 7-21 5-12 |
| * | 17 | 7:30 PM | | @ | Nebraska Wesleyan | W-72-60 | | | 8-21 6-12 |
| | 24 | 8:00 PM | | @ | Dordt | L-70-88 | | | 8-22 |
| | GPAC Tournament - First Round |