| Sat, Aug 25 | Whitney Young Hokum Karem | LaBagh Woods Forest Preserve | Chicago, IL | 9:00 AM | | |
| Tue, Aug 28 | St. Patrick's Boys & Girls XC Invitational | Schiller Woods | Chicago, IL | 4:30 PM | | |
| Thu, Sep 6 | Whitney Young Freshman/Novice Invitational | John Caldow Memorial Cross Country Course | Skinner Park, IL | 4:00 PM | | |
| Sat, Sep 8 | First to the Finish | Detweiller Park | Peoria, IL | 9:00 AM | | |
| Wed, Sep 12 | Lane Tech Larry Gnapp Tough XC Invite | Horner Park | Chicago, IL | 4:00 PM | | |
| Sat, Sep 15 | Connelly-Polka Saint Ignatius-Fenwick Invitational | Turtlehead Lake | Palos, IL | 8:45 AM | | |
| Wed, Sep 19 | Lane Tech Larry Gnapp Tough XC Rescheduled Date | Horner Park | Chicago, IL | 4:00 PM | | |
| Sat, Sep 22 | Whitney Young Zi Invitational | Washington Park | Chicago, IL | 9:00 AM | | |
| Tue, Sep 25 | Mather Invite 3 | Legion Park | Chicago, IL | 4:15 PM | | |
| Thu, Oct 4 | Latin Invitational | Lincoln Park | Chicago, IL | | | |
| Sun, Oct 7 | Nike North Side / South Side Challenge | Chicago Marathon | Chicago, IL | | | |
| Sat, Oct 13 | Chicago Public League City Championship | Washington Park | Chicago, IL | | | |
| Sat, Oct 20 | IHSA Class 3A Saint Ignatius Regional | Washington Park | Chicago, IL | 9:30 AM | | |
| Sat, Oct 27 | IHSA Class 3A Niles West Sectional | Niles West HS | Skokie, IL | | | |
| Sat, Nov 3 | IHSA Class AAA State XC Championship | Detweiller Park | Peoria, IL | | | |
