| Dual at Oswego East | 08/29/2019 | Oswego, IL | Oswego East - Oswego East XC Course |
| Plainfield City Championships | 08/31/2019 | Plainfield , IL | Plainfield Park District - Van Horn Woods |
| Plainfield Central (Wildcat Invitational) | 09/07/2019 | Plainfield, IL | Plainfield Central - South grounds |
| Dual at Joliet West | 09/17/2019 | Joliet, IL | Joliet West High School - Outdoor Track |
| Richard Spring Invite | 09/21/2019 | Peoria, IL | - Detweiller Park |
| Hoffman Estates Invite | 09/28/2019 | Palatine, IL | Saint Viator High School - Harper College Stadium |
| Dual Plainfield East | 10/01/2019 | Plainfield, IL | Plainfield Central - South grounds |
| Joe Mortimer Fr/So Meet | 10/03/2019 | , | - |
| Lockport F/S Meet | 10/09/2019 | Lockport, IL | Lockport - Campus |
| West Aurora Stampede | 10/12/2019 | Aurora, IL | West Aurora High School - Stuart Sports Complex |
| Inter squad Meet | 10/12/2019 | Plainfield, IL | Plainfield Central High School - Wildcat Stadium |
| SPC Conference Championship | 10/18/2019 | Channahon, IL | - Channahon Community Park |
| Team Time Trial 1 | 10/25/2019 | Plainfield, IL | Plainfield Central - South grounds |
| IHSA Regional | 10/26/2019 | Shorewood, IL | Plainfield South (IL) High School - Hammel Woods |
| Time Trial 2 | 11/01/2019 | Plainfield, IL | Plainfield Central - South grounds |
| IHSA Sectionals | 11/02/2019 | Western Springs, IL | Lyons Township High School - Lyons Twp HS - South Campus Bennett Field |
| Final Time Trial | 11/08/2019 | Plainfield, IL | Plainfield Central - South grounds |
| State Meet | 11/09/2019 | Peoria, IL | - Detweiller Park |
