*Schedule is weather-pending (and pandemic-pending for 2020) and subject to change.
| Date | Name | Opponents | Levels | Location | |
|---|---|---|---|---|---|
| Sat | 8/22 | Pre-Season Time Trial | N/A | Varsity, JV, Freshman | John Davis Titan Stadium |
| Sat | 9/5 | CSL Dual at Evanston | Evanston | Varsity, JV, Sophomore, Freshmen | Evanston Township High School |
| Fri | 9/11 | CSL Dual vs. Maine South | Maine South | Varsity, JV | Glenbrook South High School |
| Sat | 9/12 | CSL Dual vs. Maine South | Maine South | Freshmen, Sophomore | Glenbrook South High School |
| Tue | 9/15 | CSL Dual vs. New Trier | New Trier | Varsity, JV1, JV2, Freshmen | Glenbrook South High School |
| Wed | 9/16 | CSL Dual vs. New Trier | New Trier | Freshmen, Sophomore | Glenbrook South High School |
| Sat | 9/26 | CSL Dual at Glenbrook North | Glenbrook North | Varsity, JV, Sophomore, Freshmen | Glenbrook North High School |
| Sat | 10/3 | CSL Dual vs. Niles West | Niles West | Varsity, JV, Sophomore, Freshmen | Glenbrook South High School |
| Sat | 10/10 | Wheeling Invite | tba | Varsity, JV1 | Heritage Park |
| Sat | 10/17 | CSL Conference Championship | Evanston, Glenbrook North, Maine South, New Trier | tba | Niles West High School |
| Sat | 10/24 | IHSA Regionals | TBA | Varsity | tba |
| Sat | 10/31 | IHSA Sectionals | tba | Invite Only | tba |