Well-rooted in the Portuguese community of Ludlow, the Pioneers have called the historic Lusitano Stadium home for the USL Second Division since their inception in 1998. The team was a success from the start, making the playoffs in the first year and capturing the USL-2 title a year later with an 18-4 record through the season and playoffs.

The club returned to the championship game in 2005, their fifth trip to the postseason, and fell short of a second title in penalty kicks. The club launched a W-League team in 2004.