| Fall XC Two Mile Time Trial | 08/11/2023 | Downers Grove, IL | Downers Grove North (IL) High School - Downers Grove North Stadium |
| EIU Showdown | 08/26/2023 | Naperville, IL | Neuqua Valley High School - Neuqua Valley High School |
| Downers Grove North v Glenbard West v York | 08/30/2023 | Glendale Heights, IL | Glenbard West High School - Camera Park |
| Racine Horlick Invitational | 09/02/2023 | Kenosha, WI | University of Wisconsin–Parkside - Wayne E. Dannehl National Cross Country Course |
| Peoria First to the Finish Invitational | 09/09/2023 | Peoria, IL | - Detweiller Park |
| Downers Grove North v Hinsdale Central v Proviso West | 09/14/2023 | Woodridge, IL | Downers Grove North HS - Green Valley Forest Preserve |
| Kaneland Larry Eddington Invite | 09/16/2023 | Kaneland, IL | Kaneland High School - KHS Outdoor Track |
| Downers Grove North v OPRF and Lyons | 09/26/2023 | Schiller Park, IL | Oak Park-River Forest HS - Schiller Woods |
| New Balance/Naperville Running Co. Twilight Invite | 10/04/2023 | Naperville, IL | Naperville North High School - Cross Country Course |
| West Suburban Conference - Silver Division | 10/14/2023 | Hillside, IL | Proviso West High School - Campus XC Course |
| PN Fast Cat F/S Invite | 10/17/2023 | Plainfield, IL | Plainfield North High School - Plainfield North Cross Country Course |
| IHSA 3A Boys Cross Country Regionals | 10/21/2023 | Western Springs, IL | Lyons Township High School - South Campus |
| IHSA 3A Boys Cross Country Sectional | 10/28/2023 | Hinsdale, IL | Hinsdale Central High School - Katherine Legge Memorial Park |
| IHSA Boys 3A Cross Cross Country State Championship | 11/04/2023 | Peoria, IL | - Detweiller Park |
| Nike Cross Country Nationals - Midwest Regionals | 11/12/2023 | Terre Haute, IN | Indiana State University - LaVern Gibson Championship Cross Country Course |
| Nike Cross Nationals | 12/02/2023 | Portland, OR | Nike - Glendoveer Golf Course |
