Stadium: Harry Della Russo Stadium Round: 1
| USA USL League Two | 2024/07/06 23:00 | Boston City FC v Western Mass Pioneers | L | 0-5 |
| USA USL League Two | 2024/06/21 23:00 | Western Mass Pioneers v Boston City FC | L | 6-1 |
| USA USL League Two | 2023/05/31 00:30 | Boston City FC v Western Mass Pioneers | L | 1-10 |
| USA USL League Two | 2022/06/10 23:00 | Western Mass Pioneers v Boston City FC | L | 3-0 |
| USA USL League Two | 2022/05/11 23:00 | Boston City FC v Western Mass Pioneers | W | 2-0 |
| USA USL League Two | 2024/07/10 20:00 | Black Rock FC v Boston City FC | W | 0-2 |
| USA USL League Two | 2024/07/06 23:00 | Boston City FC v Western Mass Pioneers | L | 0-5 |
| USA USL League Two | 2024/07/02 23:00 | Boston Bolts v Boston City FC | L | 5-1 |
| USA USL League Two | 2024/06/29 23:00 | Boston City FC v Seacoast United Phantoms | L | 0-4 |
| USA USL League Two | 2024/06/26 23:00 | Vermont Green v Boston City FC | L | 5-0 |
| USA USL League Two | 2024/06/21 23:00 | Western Mass Pioneers v Boston City FC | L | 6-1 |
| USA USL League Two | 2024/06/19 23:00 | Boston City FC v Black Rock FC | D | 1-1 |
| USA USL League Two | 2024/06/15 23:00 | AC Connecticut v Boston City FC | L | 3-2 |
| USA USL League Two | 2024/07/19 23:30 | Lionsbridge FC v Western Mass Pioneers | L | 2-1 |
| USA USL League Two | 2024/07/16 23:30 | Western Mass Pioneers v FC Motown STA | W | 3-1 |
| USA USL League Two | 2024/07/13 23:00 | Western Mass Pioneers v Vermont Green | L | 1-3 |
| USA USL League Two | 2024/07/09 23:00 | AC Connecticut v Western Mass Pioneers | W | 0-3 |
| USA USL League Two | 2024/07/06 23:00 | Boston City FC v Western Mass Pioneers | W | 0-5 |
| USA USL League Two | 2024/07/03 20:00 | Black Rock FC v Western Mass Pioneers | W | 0-1 |
| USA USL League Two | 2024/06/28 23:00 | Western Mass Pioneers v Albany Rush | W | 4-1 |
| USA USL League Two | 2024/06/21 23:00 | Western Mass Pioneers v Boston City FC | W | 6-1 |