| 1 | 4021 | 9/7/19 10:30am | Field of Dreams 9v9 | Plainville Tornado | 8 - 2 | Milford-Hopedale Raiders | |
| 2 | 4026 | 9/14/19 9:00am | Kallander | Southboro Surf | 1 - 10 | Plainville Tornado | |
| 3 | 4027 | 9/21/19 10:30am | Esposito Realty Group Field - 1B | Mansfield Hornets II | 0 - 1 | Plainville Tornado | |
| 4 | 4031 | 9/28/19 10:30am | Field of Dreams 9v9 | Plainville Tornado | 6 - 2 | Medway Mustangs | |
| 5 | 4034 | 10/5/19 10:30am | Friends 2 9v9 | Foxboro Warriors | 2 - 5 | Plainville Tornado | |
| 6 | 4006 | 10/26/19 2:30pm | Field of Dreams 7v7 | Plainville Tornado | 4 - 0 | D-S Thunder | |
| 7 | 4010 | 10/19/19 10:30am | Gunning (Windsor Woods) 9v9 Field | Canton Arsenal | 1 - 5 | Plainville Tornado | |
| 8 | 4012 | 10/26/19 10:30am | Field of Dreams 9v9 | Plainville Tornado | 6 - 0 | D-S Strikers | |
| 9 | 4016 | 11/2/19 10:30am | Pope John Paul II Park | Dorchester Cyclones | 2 - 6 | Plainville Tornado | |
| 10 | 4018 | 11/9/19 10:30am | Field of Dreams 9v9 | Plainville Tornado | 6 - 1 | South End Stars | |
