| Home Meet (vs. Timothy Christian) (08/31/1999) | 3 Mile | 19:07.0 | 3 | |
| Plainfield Invitational (09/04/1999) | 3 Mile | 18:13.0 | 32 | |
| Away Meet (vs. Montini and St. Francis) (09/07/1999) | 3 Mile | 18:41.0 | 13 | |
| Sandwich Invitational (09/11/1999) | 2.95 Miles | 17:53.0 | 32 | |
| Home Meet (vs. Sycamore and Yorkville) (09/14/1999) | 3 Mile | 18:12.0 | 9 | |
| Kaneland (Larry Eddington Invitational) (09/18/1999) | 3 Mile | 18:24.0 | 57 | |
| Away Meet (vs. Evergreen Park and Ridgewood) (09/21/1999) | 3 Mile | 18:37.0 | 5 | |
| Aurora Central Catholic (Charger Classic) (09/25/1999) | 2.9 Miles | 17:09.0 | 36 | |
| Away Meet (vs. Elmwood Park and Riverside-Brookfield) (09/28/1999) | 3 Mile | 17:50.0 | 3 | |
| Lisle (Mane Event) (10/02/1999) | 5k | 18:37.0 | 74 | |
| Away Meet (vs. Lemont and Kaneland) (10/05/1999) | 5k | 19:05.0 | 17 | |
| Amboy (Columbus Day Invitational) (10/11/1999) | 2.9 Miles | 17:42.0 | 102 | |
| Suburban Prairie (White Division) Conference Championship (10/15/1999) | 3 Mile | 18:14.0 | 26 | |
| IHSA Class A Aurora Central Catholic Regional (10/23/1999) | 2.9 Miles | 16:59.0 | 19 | |
| IHSA Class A Lisle Sectional (10/30/1999) | 3 Mile | 17:50.0 | 76 | |
