| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 4:30 PM | Varsity | Scrimmage | Normal | Home | | | | | Greenwich High School - Cardinal Stadium | |
| SAT 9/2 | 10:00 AM | Varsity | Scrimmage | Normal | Away | Notre Dame-West Haven | | | | Notre Dame High School - Side Turf | 8:00 AM - 1 Bus |
| THU 9/7 | 5:15 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 2-1 | | Greenwich High School - Cardinal Stadium | |
| TUE 9/12 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Win | 6-2 | | Fairfield Ludlowe High School - Taft Field | 4:45 PM - 1 Bus |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Win | 3-0 | | St. Joseph High School - Lower Turf | 2:15 PM - 1 Bus |
| TUE 9/19 | 4:30 PM | Varsity | League | Normal | Home | Wilton | Win | 3-0 | | Greenwich High School - Cardinal Stadium | |
| THU 9/21 | 5:00 PM | Varsity | League | Normal | Home | Bridgeport Central | Win | 6-1 | | Greenwich High School - Cardinal Stadium | |
| SAT 9/23 | 10:00 AM | Varsity | League | Normal | Away | New Canaan | Win | 7-1 | | New Canaan HS - Dunning Stadium | 8:30 AM - 1 Bus |
| THU 9/28 | 4:00 PM | Varsity | League | Normal | Away | Staples | Loss | 0-2 | | Staples High School - Wakeman Field B (turf) | 2:15 PM - 1 Bus |
| SAT 9/30 | 2:15 PM | Varsity | League | Normal | Home | Trumbull | Win | 3-2 | | Greenwich High School - Cardinal Stadium | |
| WED 10/4 | 5:00 PM | Varsity | League | Normal | Home | Danbury | Win | 2-1 | | Greenwich High School - Cardinal Stadium | |
| FRI 10/6 | 4:30 PM | Varsity | League | Normal | Away | Darien | Loss | 0-1 | | Darien High School - DHS Center Oval - Turf | 3:00 PM - 1 Bus |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Home | Stamford | Tied | 0-0 | | Greenwich High School - Cardinal Stadium | |
| FRI 10/13 | 4:30 PM | Varsity | League | Normal | Home | Ridgefield | Win | 3-0 | | Greenwich High School - Cardinal Stadium | |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Home | Norwalk | Win | 3-1 | | Greenwich High School - Cardinal Stadium | |
| THU 10/19 | 4:00 PM | Varsity | League | Normal | Away | Westhill | Win | 2-1 | | Westhill High School - Front Turf | 3:00 PM - 1 Bus |
| TUE 10/24 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Tied | 0-0 | | Fairfield Warde High School - Tetreau/Davis Field | 4:45 PM - 1 Bus |
| FRI 10/27 | 4:00 PM | Varsity | Postseason | Normal | Home | Danbury | Win | 2-1 | | Greenwich High School - Cardinal Stadium | |
| MON 10/30 | 7:00 PM | Varsity | Postseason | Normal | Home | Trumbull | Loss | 4-5 | | Fairfield Ludlowe High School - Taft Field | |
| TUE 11/7 | 2:00 PM | Varsity | Postseason | Normal | Home | Bristol Central | Win | 7-1 | | Greenwich High School - Cardinal Stadium | |
| THU 11/9 | 2:30 PM | Varsity | Postseason | Normal | Home | Shelton | Win | 2-1 | | Greenwich High School - Cardinal Stadium | |
| SAT 11/11 | 2:00 PM | Varsity | Postseason | Normal | Home | Glastonbury | Win | 2-1 | | Greenwich High School - Cardinal Stadium | |
| WED 11/15 | 6:00 PM | Varsity | Postseason | Normal | Home | Stamford | Loss | 0-3 | | Norwalk High School - Ray Barry Field - Stadium | |