| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Cheshire | | | | Mercy High School - Cross Country Course | 2:30 PM - 1 Bus - GXC will travel w/BXC |
| Mercy | | |
| Wilbur Cross | | |
| SAT 9/14 | 9:00 PM | Varsity | Non-League | Normal | Away | Wilton | | | | Allen's Meadow - XC Course | 7:00 AM - 1 Bus - GXC will travel w/BXC |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | North Haven | | | | Hamden Middle School - Back Field | 2:30 PM - 1 Bus - GXC will travel w/BXC |
| Hamden | | |
| Lyman Hall | | |
| WED 10/2 | 3:30 PM | Varsity | Postseason | Normal | Home | | | | | Guilford High School - Guilford Fair grounds | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Home | Lauralton Hall | | | | Guilford High School - East River Preserve | |
| Career Magnet | | |
| Shelton | | |
| WED 10/16 | 1:30 PM | Varsity | Postseason | Normal | Home | | | | | Guilford High School - East Shore Park, New Haven | |
| SAT 10/26 | 1:00 PM | Varsity | Postseason | Normal | Away | | | | | Not Listed | 10:30 AM - 1 Bus - GXC will travel w/BXC |
| THU 10/31 | 1:00 PM | Varsity | Postseason | Normal | Away | | | | | Not Listed | 11:30 AM - 1 Bus |
| SAT 11/9 | 1:00 PM | Varsity | Postseason | Normal | Away | | | | | Not Listed | 9:00 AM - 1 Bus |