| Antioch Quad (09/01/2009) | 3 Mile | 20:14.0 | 21 | |
| Horlick Invite (09/05/2009) | 2.5 Mile Run | 16:09.0 | 15 | |
| Lake Forest Dual (09/08/2009) | 3 Mile | 21:03.0 | 19 | |
| Maine East Invite (09/12/2009) | 2.1 Miles | 12:45.0 | 1 | |
| Lakes Dual (09/14/2009) | 3 Mile | 19:38.0 | 17 | |
| Warren Invitational (09/19/2009) | 3 Mile | 18:19.0 | 119 | |
| Oak Park/River Forest Invite (09/26/2009) | 3 Mile | 19:36.0 | 73 | |
| North Chicago/Waukegan (09/28/2009) | 3 Mile | 18:30.0 | 10 | |
| Harland (Antioch) Cross Country Invite (10/03/2009) | 3 Mile | 19:21.0 | 28 | |
| Round Lake/Wauconda (10/05/2009) | 3 Mile | 19:43.0 | 13 | |
| Benet Invte (10/10/2009) | 3 Mile | 19:37.0 | 47 | |
| NSC Conference Meet (10/17/2009) | 3 Mile | 20:05.0 | 87 | |
| Prospect Invite (10/20/2009) | 2.5 Mile Run | 15:17.0 | 23 | |
| IHSA 2A Boy's Cross Country Regionals (10/24/2009) | 3 Mile | 20:05.0 | 43 | |
