| 1 | 5493 | 9/11/21 10:30am | Ryan Connolly Field 11v11 | Winchester Lionesses | 0 - 0 | Wellesley Pride | |
| 2 | 5495 | 9/18/21 10:30am | Thorndike Field 1 | Arlington G8 Courage | 0 - 6 | Winchester Lionesses | |
| 3 | 5498 | 9/25/21 10:30am | McDonald Field 11v11 | Winchester Lionesses | 2 - 1 | Winchester Flash | |
| 4 | 5501 | 10/2/21 10:30am | Fessenden B / Kumin-Loring | Newton G Cosmos | 1 - 5 | Winchester Lionesses | |
| 5 | 5503 | 10/9/21 10:30am | Ryan Connolly Field 11v11 | Winchester Lionesses | 0 - 1 | Arlington G8 Hericanes | |
| 6 | 5508 | 10/16/21 9:00am | Elm Bank 1 | Wellesley Pride | 0 - 1 | Winchester Lionesses | |
| 7 | 5511 | 10/23/21 10:30am | McDonald Field 11v11 | Winchester Lionesses | 2 - 0 | Natick Thunder | |
| 8 | 5512 | 10/31/21 10:00am | Field House Indoor 11v11 | Winchester Flash | 2 - 3 | Winchester Lionesses | |
| 9 | 5515 | 11/6/21 10:30am | McDonald Field 11v11 | Winchester Lionesses | 2 - 1 | Newton G Cosmos | |
| 10 | 5520 | 11/13/21 10:30am | AC Turf | Arlington G8 Hericanes | 0 - 2 | Winchester Lionesses | |
