| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/30 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Darien | | | | Nathan Hale MS - Callahan Complex at Nathan Hale Lower | |
| SAT 9/2 | 10:00 AM | Varsity | Scrimmage | Normal | Home | Fairfield Warde | | | | Norwalk High School - Testa Field | |
| THU 9/7 | 6:30 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 6-0 | | Norwalk High School - Testa Field | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Win | 6-2 | | New Canaan HS - Dunning Stadium | 2:30 PM - w/JV |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Greenwich | Loss | 1-6 | | Greenwich High School - Field 3 | 2:30 PM - w/JV |
| FRI 9/22 | 6:30 PM | Varsity | League | Normal | Home | Wilton | Win | 2-1 | | Norwalk High School - Testa Field | |
| TUE 9/26 | 4:00 PM | Varsity | League | Normal | Away | Darien | Loss | 1-3 | | Darien High School - DHS Stadium Field | 2:30 PM - w/JV |
| THU 9/28 | 6:30 PM | Varsity | League | Normal | Home | Trumbull | Loss | 2-3 | | Norwalk High School - Testa Field | |
| SAT 9/30 | 1:00 PM | Varsity | Non-League | Normal | Away | Amity | Win | 4-0 | | Amity Regional High School - William Johnson Stadium Field | 11:00 AM - w/JV |
| MON 10/2 | 6:30 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Win | 2-0 | | Norwalk High School - Testa Field | |
| WED 10/4 | 4:00 PM | Varsity | League | Normal | Away | Staples | Loss | 1-6 | | Staples High School - Ginny Parker Field | 2:30 PM - w/JV |
| SAT 10/7 | 2:00 PM | Varsity | Non-League | Normal | Home | Guilford | Win | 2-1 | | Norwalk High School - Testa Field | |
| WED 10/11 | 7:00 PM | Varsity | League | Normal | Away | Danbury | Win | 4-0 | | Danbury High School - Stadium Turf Field | 2:00 PM - w/JV |
| SAT 10/14 | 9:00 AM | Varsity | League | Normal | Away | Westhill | Win | 6-0 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 10/17 | 6:30 PM | Varsity | League | Normal | Home | Fairfield Warde | Win | 3-0 | | Norwalk High School - Testa Field | |
| WED 10/18 | 3:00 PM | Varsity | League | Normal | Away | St. Joseph | Win | 7-0 | | St. Joseph High School - Lower Turf | 2:30 PM - w/JV |
| FRI 10/20 | 6:30 PM | Varsity | League | Normal | Home | Ridgefield | Loss | 1-2 | | Norwalk High School - Testa Field | |
| TUE 10/24 | 7:00 PM | Varsity | League | Normal | Home | Stamford | Win | 2-0 | | Norwalk High School - Testa Field | |
| FRI 10/27 | 3:30 PM | Varsity | Postseason | Normal | Away | Ridgefield | | | | Ridgefield High School - Tiger Hollow Stadium | 1:00 PM |
| FRI 11/3 | 3:45 PM | Varsity | Scrimmage | Normal | Home | New Canaan | | | | Nathan Hale MS - Callahan Complex at Nathan Hale Lower | |
| WED 11/8 | 6:00 PM | Varsity | Postseason | Normal | Away | Hall | Win | 3-1 | | Hall High School - Stadium (Turf Field) | |
| FRI 11/10 | 4:00 PM | Varsity | Postseason | Normal | Away | Darien | Loss | 0-4 | | Darien High School - DHS Stadium Field | |