Head to Head
| USA - USL League Two | 2019/05/24 23:30 | Western Mass Pioneers v GPS Portland Phoenix | L | 1-0 |
| USA USL PDL | 2018/07/15 22:00 | GPS Portland Phoenix v Western Mass Pioneers | L | 2-3 |
| USA USL PDL | 2018/05/25 23:30 | Western Mass Pioneers v GPS Portland Phoenix | D | 1-1 |
| USA USL PDL | 2017/06/11 22:00 | GPS Portland Phoenix v Western Mass Pioneers | L | 1-2 |
| USA USL PDL | 2017/05/26 23:30 | Western Mass Pioneers v GPS Portland Phoenix | L | 2-0 |
Home History
| 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 16:00 | AC Connecticut v GPS Portland Phoenix | W | 0-2 |
| USA - USL League Two | 2019/05/31 23:00 | Black Rock FC v GPS Portland Phoenix | W | 3-4 |
| USA - USL League Two | 2019/05/24 23:30 | Western Mass Pioneers v GPS Portland Phoenix | L | 1-0 |
| USA - USL League Two | 2019/05/19 20:00 | GPS Portland Phoenix v Black Rock FC | L | 0-2 |
| USA - USL League Two | 2019/05/18 22:00 | GPS Portland Phoenix v Manhattan SC | W | 2-0 |
| USA - USL League Two | 2019/05/16 00:00 | Boston Bolts v GPS Portland Phoenix | W | 0-1 |
| USA - USL League Two | 2019/05/11 22:00 | GPS Portland Phoenix v Seacoast United Phantoms | W | 1-0 |
Away History
| 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 |
| USA - USL League Two | 2019/05/19 20:00 | Seacoast United Phantoms v Western Mass Pioneers | W | 0-2 |
| USA - USL League Two | 2019/05/17 23:00 | AC Connecticut v Western Mass Pioneers | D | 0-0 |
| USA USL PDL | 2018/07/15 22:00 | GPS Portland Phoenix v Western Mass Pioneers | W | 2-3 |
| USA USL PDL | 2018/07/13 23:30 | Western Mass Pioneers v AC Connecticut | W | 3-0 |
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