| Thu, Sep 6 | Whitney Young Freshman/Novice Invitational | John Caldow Memorial Cross Country Course | Skinner Park, IL | 4:00 PM | | |
| Sat, Sep 8 | Gordon Tech Invitational | Horner Park | Chicago, IL | | | |
| Wed, Sep 12 | Lane Tech Larry Gnapp Tough XC Invite | Horner Park | Chicago, IL | 4:00 PM | | |
| Thu, Sep 27 | Developmental Meet | Horner Park | Chicago, IL | | | |
| Sat, Sep 29 | Harlan Invite | Abbott Park | Chicago, IL | 10:00 AM | | |
| Wed, Oct 3 | 4th Annual Brooks City Prep Invite | Gwendolyn Brooks HS | Chicago, IL | 5:00 PM | | |
| Thu, Oct 4 | Latin Invitational | Lincoln Park | Chicago, IL | | | |
| Sat, Oct 13 | Chicago Public League City Championship | Washington Park | Chicago, IL | | | |
| Sat, Oct 20 | Regional | TBA | TBA, IL | 10:00 AM | | |
| Sat, Oct 20 | IHSA Class 3A Lyons Township Regional | Lyons Township South Campus | Western Springs, IL | | | |
| Sat, Oct 27 | IHSA Class 3A Normal Community Sectional | Maxwell Park | Normal, IL | 10:30 AM | | |
| Sat, Nov 3 | IHSA Class AAA State XC Championship | Detweiller Park | Peoria, IL | | | |
