| Sat, Aug 25 | Whitney Young Hokum Karem | LaBagh Woods Forest Preserve | Chicago, IL | 9:00 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 | | |
| Wed, Oct 3 | 4th Annual Brooks City Prep Invite | Gwendolyn Brooks HS | Chicago, IL | 5:00 PM | | |
| 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 2A Riverside-Brookfield Regional | Sundown Meadows | LaGrange, IL | | | |
| Sat, Oct 27 | IHSA Class 2A Wheaton Academy Sectional | Reed Keppler Park | West Chicago, IL | | | |
