Head to Head
| USA USL League Two | 2019/06/01 23:30 | Westchester Flames v Western Mass Pioneers | W | 1-5 |
| USA USL PDL | 2018/06/30 23:30 | Western Mass Pioneers v Westchester Flames | D | 1-1 |
| USA USL PDL | 2018/05/12 23:30 | Westchester Flames v Western Mass Pioneers | L | 2-0 |
| USA USL PDL | 2017/07/14 23:30 | Western Mass Pioneers v Westchester Flames | W | 7-0 |
| USA USL PDL | 2017/06/17 23:30 | Westchester Flames v Western Mass Pioneers | W | 0-4 |
| USA USL PDL | 2017/05/21 20:00 | Western Mass Pioneers v Westchester Flames | W | 2-0 |
Home History
| USA USL League Two | 2019/06/22 23:25 | Western Mass Pioneers v Boston Bolts | W | 2-1 |
| USA USL League Two | 2019/06/19 23:00 | Black Rock FC v Western Mass Pioneers | W | 0-2 |
| USA USL League Two | 2019/06/14 23:30 | Western Mass Pioneers v AC Connecticut | W | 4-0 |
| USA USL League Two | 2019/06/09 22:00 | GPS Portland Phoenix v Western Mass Pioneers | D | 1-1 |
| USA USL League Two | 2019/06/05 23:00 | Western Mass Pioneers v Black Rock FC | W | 2-0 |
| USA USL League Two | 2019/06/01 23:30 | Westchester Flames v Western Mass Pioneers | W | 1-5 |
| USA USL League Two | 2019/05/30 00:00 | Boston Bolts v Western Mass Pioneers | W | 0-4 |
| USA USL League Two | 2019/05/24 23:30 | Western Mass Pioneers v GPS Portland Phoenix | W | 1-0 |
Away History
| USA USL League Two | 2019/06/23 16:00 | AC Connecticut v Westchester Flames | W | 0-3 |
| USA USL League Two | 2019/06/19 23:30 | Westchester Flames v Manhattan SC | L | 0-3 |
| USA USL League Two | 2019/06/15 23:30 | Westchester Flames v Black Rock FC | L | 0-4 |
| USA USL League Two | 2019/06/09 22:00 | Seacoast United Phantoms v Westchester Flames | W | 1-5 |
| USA USL League Two | 2019/06/08 22:00 | GPS Portland Phoenix v Westchester Flames | D | 2-2 |
| USA USL League Two | 2019/06/01 23:30 | Westchester Flames v Western Mass Pioneers | L | 1-5 |
| USA USL League Two | 2019/05/26 18:00 | Boston Bolts v Westchester Flames | L | 1-0 |
| USA USL League Two | 2019/05/22 23:30 | Westchester Flames v AC Connecticut | D | 1-1 |