| | Day | Time | | Opponent | Score | | Record |
| November |
| | 3 | 5:30PM | @ | Briar Cliff University | W-68-63 | | 1-0 |
| | 4 | 3:00PM | @ | Grace Bible College | W-90-89 (2OT) | | 2-0 |
| | 7 | 7:30PM | vs. | Central Methodist University | L-93-94 (2OT) | | 2-1 |
| | Second consecutive double-overtime game for William Penn |
| | 10 | 7:00PM | vs. | Graceland University | W-82-62 | | 3-1 |
| | 14 | 7:00PM | vs. | Dana College | W-90-87 | | 4-1 |
| | 17 | 6:00PM | vs. | University of Wisconsin-River Falls | L-89-101 | | 4-2 |
| | 18 | 6:00PM | vs. | Dakota State University | W-93-78 | | 5-2 |
| | Bethel Tournament |
| | 25 | 7:30PM | @ | Knox College | L-75-79 | | 5-3 |
| | 26 | 3:00PM | @ | Monmouth College | L-73-86 | | 5-4 |
| | 28 | 7:30PM | @ | Missouri Valley College | L-67-82 | | 5-5 |
| December |
| | 8 | 7:30PM | vs. | Peru State College | W-70-54 | | 6-5 |
| | 9 | 5:00PM | vs. | University of Illinois at Springfield | W-93-88 | | 7-5 |
| | 15 | 7:00PM | vs. | Calvary Bible College | W-106-63 | | 8-5 |
| | 29 | | vs. | Baker University | L-69-84 | | 8-6 |
| | Briar Cliff Tournament |
| | 30 | 2:00PM | vs. | Haskell Indian Nations University | W-87-77 | | 9-6 |
| | Briar Cliff Tournament |
| | 31 | 6:00PM | @ | Nebraska Christian College | W-121-40 | | 10-6 |
| January |
| * | 3 | 7:30PM | @ | Waldorf | W-93-89 | | 11-6 1-0 |
| * | 6 | 3:00PM | vs. | Mount Mercy | L-60-77 | | 11-7 1-1 |
| * | 10 | 7:30PM | vs. | Grand View | W-78-64 | | 12-7 2-1 |
| * | 13 | 3:00PM | vs. | Viterbo | W-81-53 | | 13-7 3-1 |
| * | 17 | 7:30PM | @ | Iowa Wesleyan | W-74-64 | | 14-7 4-1 |
| * | 20 | 3:00PM | @ | Ashford | W-69-61 | | 15-7 5-1 |
| * | 24 | 7:30PM | vs. | St. Ambrose | W-86-72 | | 16-7 6-1 |
| * | 27 | 3:00PM | vs. | Waldorf | W-88-62 | | 17-7 7-1 |
| | Penn has now won six in a row |
| * | 31 | 7:30PM | @ | Grand View | W-65-57 | | 18-7 8-1 |
| February |
| * | 3 | 3:00PM | @ | Mount Mercy | W-76-67 | | 19-7 9-1 |
| * | 7 | 7:30PM | vs. | Iowa Wesleyan | W-76-53 | | 20-7 10-1 |
| * | 10 | 6:00PM | @ | Viterbo | W-70-58 | | 21-7 11-1 |
| * | 14 | 7:30PM | @ | St. Ambrose | L-69-70 | | 21-8 11-2 |
| * | 17 | 3:00PM | vs. | Ashford | W-82-66 | | 22-8 12-2 |
| | Penn wins Midwest Classic Conference title outright for second year in a row |
| | 21 | 7:00PM | vs. | Ashford | W-66-56 | | 23-8 |
| | Midwest Classic Conference Tournament 1st Round |
| | 26 | 7:30PM | vs. | Viterbo | W-73-71 (OT) | | 24-8 |
| | MCC Semifinals |
| | 27 | 7:00PM | vs. | Waldorf | W-75-65 | | 25-8 |
| | MCC Tournament Championship |
| March |
| | 8 | 9:15PM | vs. | Mayville State University | L-86-101 | | 25-9 |
| | NAIA Division II National Tournament (First Round) |
