Western Mass Pioneers Year-by-year Year-by-year

| Year_ | Division | League | Reg_Season | Playoffs | Open_Cup_ |
|---|---|---|---|---|---|
| 1998 | 3 | USISL D-3 Pro League | 3rd, Northeast | Division Semifinals | 2nd Round |
| 1999 | 3 | USL D-3 Pro League | 1st, Northern | Champion | Did not qualify |
| 2000 | 3 | USL D-3 Pro League | 5th, Northern | Conference Finals | Did not qualify |
| 2001 | 3 | USL D-3 Pro League | 7th, Northern | Did not qualify | Did not qualify |
| 2002 | 3 | USL D-3 Pro League | 1st, Northern | Quarterfinals | Did not qualify |
| 2003 | 3 | USL Pro Select League | 3rd, Northern | Did not qualify | Did not qualify |
| 2004 | 3 | USL Pro Soccer League | 3rd, Northern | Did not qualify | 2nd Round |
| 2005 | 3 | USL Second Division | 1st | Final | 3rd Round |