| Wed, Sep 2 | St. Patrick Invitational | Schiller Park | Chicago, IL | | | |
| Wed, Sep 16 | Lane Tech XC Invitational | Clark Park | Chicago, IL | 4:00 PM | | |
| Sat, Sep 19 | Richard Spring Invitational | Detweiller Park | Peoria, IL | | | |
| Tue, Sep 22 | U High Midway Miles # 2 | Washington Park | Chicago, IL | 4:30 PM | | |
| Sat, Sep 26 | Whitney Young "ZI" XC Invite | Oglesby Grove | Chicago, IL | 9:00 AM | | |
| Thu, Oct 8 | LT/ Belding Elementary Meet | Clark Park | Chicago, IL | 4:30 PM | | |
| Sun, Oct 11 | Chicago Marathon XC Invitational | 31st & Michigan | Chicago, IL | 7:40 AM | | |
| Sun, Oct 11 | Walt Disney World Cross Country Classic 2009 | Disney Sports Complex | Walt Disney World, FL | | | |
| Sat, Oct 17 | CPS XC Championships | Washington Park | Chicago, IL | 8:00 AM | | |
| Sat, Oct 24 | IHSA 3A & 2A Regional | Schiller Woods | Chicago, IL | 3:30 AM | | |
| Sat, Nov 7 | IHSA Class AAA State XC Championship | Detweiller Park | Peoria, IL | 1:00 PM | | |
| Sun, Nov 15 | Nike Midwest Regionals (NXN) | Lavern Gibson Championship Cross Country Course | Terre Haute, IN | | | |
| Sat, Nov 21 | Mid-East Cross Country Championships | Indian Riffle Park | Kettering, OH | | | |
| Sat, Sep 4 | Whitney Young Hokum Karem Eikiden Relay | LaBagh Woods Forest Preserve | Chicago, IL | | | |
| Sun, Oct 10 | Nike Northside Southside Challenge at the Chicago Marathon | 31st & Michigan | Chicago, IL | 7:40 AM | | |
