| Home Meet (vs. Timothy Christian) (08/31/1999) | 2.1 Miles | 14:48.0 | 5 | |
| Home Meet (vs. Timothy Christian) (08/31/1999) | 2.5 Mile Run | 20:11.0 | 7 | |
| Plainfield Invitational (09/04/1999) | 2.5 Mile Run | 18:37.0 | 36 | |
| Away Meet (vs. Montini and St. Francis) (09/07/1999) | 2.25 Miles | 19:02.0 | 16 | |
| Sandwich Invitational (09/11/1999) | 2.45 Miles | 17:34.0 | 52 | |
| Home Meet (vs. Sycamore and Yorkville) (09/14/1999) | 2.5 Mile Run | 18:42.0 | 12 | |
| Kaneland (Larry Eddington Invitational) (09/18/1999) | 2.45 Miles | 17:18.0 | 62 | |
| Away Meet (vs. Evergreen Park and Ridgewood) (09/21/1999) | 2.5 Mile Run | 18:14.0 | 3 | |
| Away Meet (vs. Elmwood Park and Riverside-Brookfield) (09/28/1999) | 2.5 Mile Run | 18:16.0 | 6 | |
| Lisle (Mane Event) (10/02/1999) | 4k | 17:57.0 | 78 | |
| Away Meet (vs. Lemont and Kaneland) (10/05/1999) | 2.25 Miles | 16:15.0 | 12 | |
| Amboy (Columbus Day Invitational) (10/11/1999) | 2.45 Miles | 16:54.0 | 84 | |
| Suburban Prairie (White Division) Conference Championship (10/15/1999) | 2.45 Miles | 16:36.0 | 18 | |
| IHSA Class A Aurora Central Catholic Regional (10/23/1999) | 2.1 Miles | 14:40.0 | 15 | |
| IHSA Class A Lisle Sectional (10/30/1999) | 4k | 17:51.0 | 71 | |
