| Sim Time | Game Date | Type | Visiting Team | Home Team | Result | Game Action | Attendance |
|---|---|---|---|---|---|---|---|
| Mon Sep 22nd | October 8th | Exhibition | West Virginia Wesleyan | University of Chicago | W 75 - 90 | (play) | 2,279 |
| Tue Sep 23rd | October 10th | Exhibition | Maryville | University of Chicago | W 74 - 88 | (play) | 2,518 |
| Wed Sep 24th | October 12th | Exhibition | University of Chicago | Marietta College | W 78 - 63 | (play) | 428 |
| Thu Sep 25th | October 16th | Non-Conference | University of Chicago | IU Indianapolis | W 98 - 89 | (play) | 6,186 |
| Fri Sep 26th | October 19th | Non-Conference | University of Chicago | Middle Tennessee State | L 68 - 72 | (play) | 5,000 |
| Sat Sep 27th | October 23rd | Non-Conference | Wisconsin Lutheran | University of Chicago | W 68 - 72 | (play) | 4,617 |
| Sun Sep 28th | October 26th | Non-Conference | Davidson | University of Chicago | W 75 - 82 | (play) | 4,330 |
| Mon Sep 29th | October 30th | Non-Conference | #4 Gardner-Webb | University of Chicago | L 96 - 63 | (play) | 4,754 |
| Tue Sep 30th | November 2nd | Non-Conference | University of Chicago | College of Charleston | L 64 - 76 | (play) | 3,285 |
| Wed Oct 1st | November 6th | Non-Conference | University of Chicago | La Salle | L 75 - 94 | (play) | 4,326 |
| Thu Oct 2nd | November 9th | Non-Conference | Bates | University of Chicago | L 90 - 57 | (play) | 4,737 |
| Fri Oct 3rd | November 13th | Non-Conference | Georgia State | University of Chicago | L 87 - 82 (ot) | (play) | 4,875 |
| Sat Oct 4th | November 16th | Non-Conference | University of Chicago | Wartburg | W 75 - 61 | (play) | 942 |
| Sun Oct 5th | November 21st | Conference | Idaho | University of Chicago | L 88 - 78 | (play) | 5,000 |
| Mon Oct 6th | November 23rd | Conference | Winthrop | University of Chicago | W 65 - 91 | (play) | 5,000 |
| Tue Oct 7th | November 28th | Conference | University of Chicago | Wisconsin-Stout | L 60 - 77 | (play) | 4,226 |
| Wed Oct 8th | November 30th | Conference | University of Chicago | Tulsa | L 61 - 87 | (play) | 5,000 |
| Thu Oct 9th | December 5th | Conference | Cal Poly | University of Chicago | W 71 - 92 | (play) | 4,441 |
| Fri Oct 10th | December 7th | Conference | UPR Bayamón | University of Chicago | L 99 - 74 | (play) | 4,846 |
| Sat Oct 11th | December 12th | Conference | University of Chicago | Franklin | L 57 - 65 | (play) | 5,000 |
| Sun Oct 12th | December 14th | Conference | San Diego | University of Chicago | W 68 - 75 | (play) | 4,505 |
| Mon Oct 13th | December 19th | Conference | Savannah State | University of Chicago | L 82 - 72 | (play) | 4,137 |
| Tue Oct 14th | December 21st | Conference | Central State | University of Chicago | L 95 - 60 | (play) | 4,760 |
| Wed Oct 15th | December 26th | Conference | San Francisco State | University of Chicago | L 82 - 63 | (play) | 4,300 |
| Thu Oct 16th | December 28th | Conference | SUNY Potsdam | University of Chicago | W 61 - 86 | (play) | 4,014 |
| Fri Oct 17th | January 2nd | Conference | University of Chicago | Hampden-Sydney | L 78 - 117 | (play) | 3,907 |
| Sat Oct 18th | January 4th | Conference | University of Chicago | Kean University | L 57 - 65 | (play) | 4,169 |
| Sun Oct 19th | January 9th | Conference | University of Chicago | Norfolk State | L 64 - 69 | (play) | 3,985 |
| Mon Oct 20th | January 11th | Conference | University of Chicago | Idaho | W 91 - 78 | (play) | 5,000 |
| Tue Oct 21st | January 16th | Conference | University of Chicago | Winthrop | L 68 - 76 | (play) | 2,251 |
| Wed Oct 22nd | January 18th | Conference | Wisconsin-Stout | University of Chicago | W 61 - 71 | (play) | 3,450 |
| Thu Oct 23rd | January 23rd | Conference | Tulsa | University of Chicago | W 57 - 63 | (play) | 4,131 |
| Fri Oct 24th | January 25th | Conference | University of Chicago | Cal Poly | L 75 - 82 | (play) | 4,814 |
| Sat Oct 25th | January 30th | Conference | University of Chicago | UPR Bayamón | L 50 - 74 | (play) | 3,232 |
| Sun Oct 26th | February 1st | Conference | Franklin | University of Chicago | W 53 - 80 | (play) | 3,830 |
| Mon Oct 27th | February 6th | Conference | University of Chicago | San Diego | L 56 - 103 | (play) | 2,804 |
| Tue Oct 28th | February 8th | Conference | University of Chicago | Savannah State | L 60 - 94 | (play) | 5,000 |
| Wed Oct 29th | February 13th | Conference | University of Chicago | Central State | L 65 - 93 | (play) | 5,000 |
| Thu Oct 30th | February 15th | Conference | University of Chicago | San Francisco State | L 79 - 87 | (play) | 5,000 |
| Fri Oct 31st | February 20th | Conference | University of Chicago | SUNY Potsdam | W 88 - 76 | (play) | 2,582 |
| Sat Nov 1st | February 22nd | Conference | Hampden-Sydney | University of Chicago | W 76 - 88 | (play) | 3,394 |
| Sun Nov 2nd | February 27th | Conference | Kean University | University of Chicago | W 49 - 71 | (play) | 3,249 |
| Mon Nov 3rd | February 29th | Conference | Norfolk State | University of Chicago | L 91 - 72 | (play) | 3,614 |
| Tue Nov 4th | March 5th | Playoff | University of Chicago | Tulsa | W 79 - 77 | (play) | 8,566 |
| Wed Nov 5th | March 6th | Playoff | University of Chicago | Idaho | L 61 - 83 | (play) | 8,564 |
| Sat Nov 8th | March 12th | Invitational | University of Chicago | Northwestern State | L 60 - 62 | (play) | 8,106 |
| Sun Nov 9th | March 14th | Invitational | Occidental College | University of Chicago | W 55 - 77 | (play) | 8,272 |
| Mon Nov 10th | March 19th | Invitational | Maranatha Baptist University | University of Chicago | W 63 - 88 | (play) | 8,412 |
| Tue Nov 11th | March 21st | Invitational | University of Chicago | Mississippi College | W 97 - 82 | (play) | 8,098 |
| Wed Nov 12th | March 28th | Invitational | University of Chicago | Utah State | L 65 - 91 | (play) | 8,094 |