1998-99 St. Olaf College Men's Basketball Schedule
| DATE | OPPONENT | LOCATION | SCORE |
| Nov. 20 | Grandview College | Waverly, Iowa | L 73-69 |
| Nov. 21 | Blackburn College | Waverly, Iowa | W 87-62 |
| Nov. 30 | University of Minnesota - Morris | Home | W 53-52 |
| Dec. 5 | Macalester College | St. Paul, Minn. | W 61-53 |
| Dec. 9 | Saint John's University | Home | W 81-72 |
| Dec. 12 | Northwestern College | St. Paul, Minn. | W 68-58 |
| Jan. 2 | University of St. Thomas | Home | L 66-60 |
| Jan. 4 | Saint Mary's University | Winona, Minn. | L 68-57 |
| Jan. 6 | Gustavus Adolphus College | St. Peter, Minn. | W 87-64 |
| Jan. 9 | Bethel University | Home | L 75-65 (OT) |
| Jan. 11 | Concordia College-Moorhead | Moorhead, Minn. | W 77-72 |
| Jan. 13 | Augsburg College | Minneapolis, Minn. | L 75-69 |
| Jan. 16 | Hamline University | St. Paul, Minn. | W 63-50 |
| Jan. 20 | Carleton College | Home | W 63-59 |
| Jan. 23 | Macalester College | Home | W 73-64 |
| Jan. 27 | Saint John's University | Collegeville, Minn. | L 74-60 |
| Feb. 1 | University of St. Thomas | St. Paul, Minn. | L 67-60 |
| Feb. 3 | St. Mary's University | Home | W 69-57 (OT) |
| Feb. 6 | Gustavus Adolphus College | Home | L 69-55 |
| Feb. 10 | Bethel University | Arden Hills, Minn. | L 70-64 |
| Feb. 13 | Concordia College-Moorhead | Home | W 68-60 |
| Feb. 15 | Augsburg College | Home | L 94-80 |
| Feb. 17 | Hamline University | Home | W 72-55 |
| Feb. 20 | Carleton College | Northfield, Minn. | L 78-53 |
