| Home Meet (vs. Timothy Christian) (08/31/1999) | 3 Mile | 18:32.0 | 2 | |
| Plainfield Invitational (09/04/1999) | 3 Mile | 18:10.0 | 30 | |
| Away Meet (vs. Montini and St. Francis) (09/07/1999) | 3 Mile | 17:32.0 | 7 | |
| Sandwich Invitational (09/11/1999) | 2.95 Miles | 17:48.0 | 30 | |
| Home Meet (vs. Sycamore and Yorkville) (09/14/1999) | 3 Mile | 17:46.0 | 5 | |
| Kaneland (Larry Eddington Invitational) (09/18/1999) | 3 Mile | 18:13.0 | 49 | |
| Away Meet (vs. Evergreen Park and Ridgewood) (09/21/1999) | 3 Mile | 17:58.0 | 4 | |
| Aurora Central Catholic (Charger Classic) (09/25/1999) | 2.9 Miles | 16:48.0 | 27 | |
| Away Meet (vs. Elmwood Park and Riverside-Brookfield) (09/28/1999) | 3 Mile | 18:34.0 | 5 | |
| Lisle (Mane Event) (10/02/1999) | 5k | 18:36.0 | 72 | |
| Away Meet (vs. Lemont and Kaneland) (10/05/1999) | 5k | 18:56.0 | 15 | |
| Amboy (Columbus Day Invitational) (10/11/1999) | 2.9 Miles | 17:29.0 | 91 | |
| Suburban Prairie (White Division) Conference Championship (10/15/1999) | 3 Mile | 18:13.0 | 25 | |
| IHSA Class A Aurora Central Catholic Regional (10/23/1999) | 2.9 Miles | 16:27.0 | 10 | |
| IHSA Class A Lisle Sectional (10/30/1999) | 3 Mile | 17:16.0 | 47 | |
