| 1 | 5491 | 9/11/21 10:30am | Fessenden B / Kumin-Loring | Newton G Cosmos | 2 - 2 | Winchester Flash | |
| 2 | 5494 | 9/18/21 10:30am | Ryan Connolly Field 11v11 | Winchester Flash | 3 - 0 | Arlington G8 Hericanes | |
| 3 | 5498 | 9/25/21 10:30am | McDonald Field 11v11 | Winchester Lionesses | 2 - 1 | Winchester Flash | |
| 4 | 5500 | 10/2/21 10:30am | McDonald Field 11v11 | Winchester Flash | 4 - 0 | Arlington G8 Courage | |
| 5 | 5505 | 10/17/21 12:00pm | Elm Bank 2 | Wellesley Pride | 0 - 1 | Winchester Flash | |
| 6 | 5506 | 10/16/21 10:30am | Ryan Connolly Field 11v11 | Winchester Flash | 3 - 1 | Newton G Cosmos | |
| 7 | 5510 | 10/23/21 10:30am | Spy Pond Field | Arlington G8 Hericanes | 3 - 4 | Winchester Flash | |
| 8 | 5512 | 10/31/21 10:00am | Field House Indoor 11v11 | Winchester Flash | 2 - 3 | Winchester Lionesses | |
| 9 | 5516 | 11/6/21 9:00am | Elm Bank Field 3 | Natick Thunder | 2 - 2 | Winchester Flash | |
| 10 | 5518 | 11/13/21 10:30am | Ryan Connolly Field 11v11 | Winchester Flash | 0 - 0 | Wellesley Pride | |
