* Conference Event
% Exhibition/Scrimmage Event
Event times are (CST)
| October |
| | 30 | 6:30PM | Holy Cross | @ | Concordia University | 53-94 | |
| November |
| * | 3 | 6:00PM | Saint Xavier | @ | Holy Cross | 94-74 | |
| | 6 | 7:00PM | Holy Cross | @ | Goshen College | 68-115 | |
| | Goshen College Tournament Nov. 6-7 |
| | 7 | 2:00PM | Holy Cross | @ | Cornerstone University | 61-98 | |
| | Goshen College Tournament Nov. 6-7 |
| | 11 | 6:00PM | Holy Cross | @ | Taylor University | 68-87 | |
| | 13 | 6:00PM | Holy Cross | vs. | Marian College | 73-71 | |
| | Bethel College Tournament |
| | 14 | 2:00PM | Holy Cross | @ | Bethel College | 61-74 | |
| | Bethel College Tournament |
| | 17 | 7:00PM | Huntington College | @ | Holy Cross | 104-75 | |
| | 21 | 4:00PM | Holy Cross | @ | Purdue North Central | 77-87 | |
| | 23 | 6:00PM | Holy Cross | @ | Davenport University | 46-105 | |
| | 25 | 8:00PM | Holy Cross | @ | Calumet St. Joseph | 81-100 | |
| December |
| * | 2 | 6:00PM | Holy Cross | @ | Saint Xavier | 65-80 | |
| | 6 | 2:00PM | Andrews University | @ | Holy Cross | 51-79 | |
| | 8 | 6:00PM | Bethel College | @ | Holy Cross | 87-63 | |
| | 16 | 6:00PM | Holy Cross | @ | University of Northwestern Ohio | 53-75 | |
| | 19 | 2:00PM | Concordia University | @ | Holy Cross | 73-70 | |
| * | 22 | 6:00PM | Holy Cross | @ | Indiana - South Bend | 76-85 | |
| January |
| * | 9 | 2:00PM | Indiana - South Bend | @ | Holy Cross | 77-61 | |
| | 16 | 4:00PM | Holy Cross | @ | Purdue Calumet | 80-73 | |
| * | 20 | 6:00PM | Holy Cross | @ | Robert Morris | 48-91 | |
| * | 23 | 2:00PM | St. Francis | @ | Holy Cross | 89-76 | |
| | 27 | 8:00PM | Trinity Christian | @ | Holy Cross | 76-69 | |
| * | 30 | 2:00PM | Olivet Nazarene | @ | Holy Cross | 94-61 | |
| February |
| | 1 | 6:00PM | Holy Cross | @ | Andrews University | 61-65 | |
| | 6 | 4:00PM | Cardinal Stritch | @ | Holy Cross | 72-55 | |
| | 8 | 7:30PM | Holy Cross | @ | Olivet Nazarene | | |
| | 10 | 8:00PM | Purdue Calumet | @ | Holy Cross | 94-82 | |
| * | 13 | 2:00PM | Robert Morris | @ | Holy Cross | 96-54 | |
| | 16 | 6:00PM | Moody Bible Institute | @ | Holy Cross | 65-58 | |
| * | 20 | 7:00PM | Holy Cross | @ | St. Francis | 52-80 | |
| * | 23 | 6:30PM | Holy Cross | @ | Olivet Nazarene | 56-97 | |
| March |
| | 2 | 7:00PM | Holy Cross | @ | Saint Xavier | 71-87 | |
| | CCAC Tournament- Quarterfinal Round |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (CST)