| Home Meet (vs. Timothy Christian) (08/31/1999) | 2.1 Miles | 16:03.0 | 29 | |
| Home Meet (vs. Timothy Christian) (08/31/1999) | 2.5 Mile Run | 22:23.0 | 11 | |
| Plainfield Invitational (09/04/1999) | 2.5 Mile Run | 21:04.0 | 58 | |
| Away Meet (vs. Montini and St. Francis) (09/07/1999) | 2.25 Miles | 20:03.0 | 23 | |
| Sandwich Invitational (09/11/1999) | 2.45 Miles | 18:31.0 | 67 | |
| Home Meet (vs. Sycamore and Yorkville) (09/14/1999) | 2.5 Mile Run | 19:54.0 | 21 | |
| Kaneland (Larry Eddington Invitational) (09/18/1999) | 2.45 Miles | 19:06.0 | 103 | |
| Away Meet (vs. Evergreen Park and Ridgewood) (09/21/1999) | 2.5 Mile Run | 19:39.0 | 7 | |
| Away Meet (vs. Elmwood Park and Riverside-Brookfield) (09/28/1999) | 2.5 Mile Run | 19:17.0 | 12 | |
| Lisle (Mane Event) (10/02/1999) | 4k | 19:06.0 | 118 | |
| Away Meet (vs. Lemont and Kaneland) (10/05/1999) | 2.25 Miles | 17:16.0 | 24 | |
| Amboy (Columbus Day Invitational) (10/11/1999) | 2.45 Miles | 18:11.0 | 155 | |
| Suburban Prairie (White Division) Conference Championship (10/15/1999) | 2.45 Miles | 17:37.0 | 38 | |
| IHSA Class A Aurora Central Catholic Regional (10/23/1999) | 2.1 Miles | 15:44.0 | 35 | |
| IHSA Class A Lisle Sectional (10/30/1999) | 4k | 18:22.0 | 89 | |
