| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 8/28 | 9:00 AM | Varsity | Scrimmage | Normal | Home | | | | | Greenwich High School - Cardinal Stadium | |
| WED 8/30 | 2:00 PM | Varsity | Scrimmage | Normal | Away | | | | | Greenwich Academy - Tammaro Field | 1:00 PM - V & JV sharing bus |
| SAT 9/2 | 9:30 AM | Varsity | Scrimmage | Normal | Home | Bethel | | | | Greenwich High School - Cardinal Stadium | |
| THU 9/7 | 6:15 PM | Varsity | League | Normal | Away | Brien McMahon | Win | 2-0 | | Brien McMahon High School - Pride Field | 4:35 PM - 1 Bus - |
| WED 9/13 | 4:30 PM | Varsity | League | Normal | Home | St. Joseph | Loss | 0-7 | | Greenwich High School - Cardinal Stadium | |
| TUE 9/19 | 6:00 PM | Varsity | League | Normal | Away | Wilton | Tied | 0-0 | | Wilton HS - Lilly Field | 4:30 PM - 1 Bus |
| WED 9/20 | 4:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 8-0 | | Bridgeport Central - Kennedy Stadium Turf | 2:30 PM - 1 Bus |
| FRI 9/22 | 4:30 PM | Varsity | League | Normal | Home | New Canaan | Win | 2-1 | | Greenwich High School - Cardinal Stadium | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | Staples | Tied | 2-2 | | Greenwich High School - Cardinal Stadium | |
| SAT 9/30 | 11:30 AM | Varsity | League | Normal | Away | Trumbull | Tied | 2-2 | | Trumbull High School - Cork Field | 3:00 PM - 1 Bus |
| TUE 10/3 | 5:00 PM | Varsity | League | Normal | Away | Danbury | Win | 2-0 | | Danbury High School - Stadium Turf Field | 3:00 PM - 1 Bus - Varsity and JV share |
| FRI 10/6 | 6:30 PM | Varsity | League | Normal | Home | Darien | Win | 5-2 | | Greenwich High School - Cardinal Stadium | |
| MON 10/9 | 4:30 PM | Varsity | League | Normal | Home | Stamford | Win | 1-0 | | Greenwich High School - Field 3 | |
| THU 10/12 | 6:00 PM | Varsity | League | Normal | Away | Ridgefield | Tied | 0-0 | | Ridgefield High School - Tiger Hollow Stadium | 4:00 PM - 1 Bus |
| MON 10/16 | 6:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 5-1 | | Norwalk High School - Testa Field | 4:00 PM - 1 Bus |
| WED 10/18 | 4:30 PM | Varsity | League | Normal | Home | Westhill | Win | 3-1 | | Greenwich High School - Cardinal Stadium | |
| FRI 10/20 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Win | 4-2 | | Greenwich High School - Cardinal Stadium | |
| MON 10/23 | 4:30 PM | Varsity | League | Normal | Home | Fairfield Warde | Win | 2-0 | | Greenwich High School - Cardinal Stadium | |
| THU 10/26 | 3:30 PM | Varsity | Postseason | Normal | Home | Darien | Loss | 0-2 | | Greenwich High School - Cardinal Stadium | |
| MON 11/6 | 2:00 PM | Varsity | Postseason | Normal | Home | West Haven | Win | 5-0 | | Greenwich High School - Cardinal Stadium | |
| WED 11/8 | 4:15 PM | Varsity | Postseason | Normal | Home | Southington | Win | 3-1 | | Greenwich High School - Cardinal Stadium | |
| FRI 11/10 | 2:00 PM | Varsity | Postseason | Normal | Away | Staples | Loss | 1-2 | | Staples High School - Wakeman Field B (turf) | 11:45 AM - 1 Bus |