2021-2022 Boys Soccer
| Date | | Opponent | Location | Result | | W/L |
|---|
| Fri, Sep 10
| | St. Joseph | Stamford HS- SHS Upp | 4-3 | | W |
| St. Joseph | Stamford HS- SHS Upp |
| Sat, Sep 11
| | Staples | Stamford HS- SHS Upp | 1-4 | | L |
| Staples | Stamford HS- SHS Upp |
| Tue, Sep 14
| | Brien McMahon | Brien McMahon HS- Ca | 0-0 | | T |
| Brien McMahon | Brien McMahon HS- Ca |
| Sat, Sep 18
| | Danbury | Danbury HS- Stadium | 0-3 | | L |
| Danbury | Danbury HS- Stadium |
| Mon, Sep 20
| | Harding | Warren Harding HS- L | 7-0 | | W |
| Harding | Warren Harding HS- L |
| Wed, Sep 22
| | Fairfield Warde | Home- Boyle Stadium | 0-2 | | L |
| Fairfield Warde | Home- Boyle Stadium |
| Fri, Sep 24
| | Wilton | Wilton HS- Lilly Fie | 0-2 | | L |
| Wilton | Wilton HS- Lilly Fie |
| Tue, Sep 28
| | New Canaan | Home- Boyle Stadium | 4-0 | | W |
| New Canaan | Home- Boyle Stadium |
| Fri, Oct 01
| | Ridgefield | Ridgefield HS- Tiger | 2-5 | | L |
| Ridgefield | Ridgefield HS- Tiger |
| Tue, Oct 05
| | Trumbull | Trumbull HS- Cork Fi | 0-4 | | L |
| Trumbull | Trumbull HS- Cork Fi |
| Thu, Oct 07
| | Fairfield Ludlowe | Stamford HS- SHS Upp | 3-1 | | W |
| Fairfield Ludlowe | Stamford HS- SHS Upp |
| Wed, Oct 13
| | Westhill | Stamford HS- SHS Upp | 1-1 | | T |
| Westhill | Stamford HS- SHS Upp |
| Sat, Oct 16
| | Norwalk | Norwalk HS- Testa Fi | 0-7 | | L |
| Norwalk | Norwalk HS- Testa Fi |
| Tue, Oct 19
| | Darien | Stamford HS- SHS Upp | 1-4 | | L |
| Darien | Stamford HS- SHS Upp |
| Fri, Oct 22
| | Bridgeport Central | Bridgeport Central H | 3-0 | | W |
| Bridgeport Central | Bridgeport Central H |
| Tue, Oct 26
| | Greenwich | Stamford HS- SHS Upp | 1-3 | | L |
| Greenwich | Stamford HS- SHS Upp |
