*Schedule is subject to change.
| Date | Name | Opponents | Levels | Location | |
|---|---|---|---|---|---|
| Sat | 8/22 | Pre-Season Time Trial TT | Varsity, JV, Freshman | John Davis Titan Stadium | |
| Sat | 9/5 | CSL Dual at Evanston CSL | Evanston | Varsity, JV1, JV2, Freshmen | Evanston Township High School |
| Fri | 9/11 | CSL Dual vs. Maine South CSL | Maine South | Varsity, JV1 | Glenbrook South High School |
| Sat | 9/12 | CSL Dual vs. Maine South CSL | Maine South | Freshmen, JV2 | Glenbrook South High School |
| Tue | 9/15 | CSL Dual vs. New Trier CSL | New Trier | Varsity, JV1 | Glenbrook South High School |
| Wed | 9/16 | CSL Dual vs. New Trier CSL | New Trier | Freshmen, JV2 | Glenbrook South High School |
| Sat | 9/26 | CSL Dual at Glenbrook North CSL | Glenbrook North | Varsity, JV, Sophomore, Freshman | Glenbrook North High School |
| Sat | 10/3 | CSL Dual vs. Niles West CSL | Niles West, Loyola Academy | Varsity, JV1, JV2, Freshmen | Glenbrook South High School |
| Sat | 10/10 | Wildcat Invitational | Conant, Maine West, Northridge Prep, Palatine, Wheeling | Varsity, JV1 | Heritage Park |
| Mon | 10/12 | CSL South Boys JV Cross Country Championship CSL | CSL South | Junior Varsity | Duke Childs Field |
| Mon | 10/12 | CSL South Boys Frosh Cross Country Championship CSL | CSL South | Frosh | New Trier Northfield |
| Sat | 10/17 | CSL South Conference Championship CSL | CSL South | Varsity | Duke Childs Field |
| Sat | 10/24 | Hoffman Estates (H.S.) Regional IHSA | Maine West, Elk Grove, Evanston, Conant, Hoffman Estates, Prospect, Maine East, Rolling Meadows, Schaumburg, Niles North | Varsity | Hoffman Estates High School |
| Sat | 10/31 | Hoffman Estates (H.S.) Sectional IHSA | Hersey, Barrington, Cary-Grove, Maine West, Evanston, Grant, Warren, Highland Park, Hoffman Estates, Lake Zurich, Libertyville, Prospect, Loyola Academy, New Trier, Individual Qualifiers | Invite Only | Hoffman Estates High School |
| Thu | 11/5 | Post-Season Time Trial TT | All Levels | John Davis Titan Stadium |