The Massachusetts Pirates joined the IFL after leaving the NAL. Alejandro Bennefield passed for 1,972 yards, 43 touchdowns and ten interceptions; he also ran for 19 touchdowns and 286 yards. Thomas Owens led all receivers with 1,014 yards and 27 scores. Justin Stockton rushed for 528 yards and twelve touchdowns. Da'Sean Downey racked up 5.5 sacks on the defensive end. The team only fumbled nine times on the entire year, while forcing 14 turnovers from opponents on 29 fumbles. The Pirates would cruise through the playoffs and end up in Arizona against the Rattlers for the United Bowl. After Arizona tied the game with ten seconds left in regulation, Massachusetts won on an overtime field goal 37-34. Bennefield returned for ten games in 2022, throwing for 1,382 yards, 28 touchdowns and five picks. Thomas Owens caught 67 balls for 936 yards and 22 touchdowns. The Pirates went 11-5 on the regular season, winning several close games against Sioux Falls, Frisco, Bismarck, and Quad City. In the first round of the playoffs, Massachusetts hosted Quad City. The game went to overtime and the Pirates scored first, but missed the extra point. Quad City scored and the extra point was good, giving them the 39-38 victory. The franchise returned in 2023 with more success, going 9-6 in the regular season and qualifying for the playoffs. The Pirates were undefeated at home, making the DCU Center one of the toughest places to play in the league. Tony Russo quarterbacked the team, passing for 2,243 yards, 49 touchdowns and eleven interceptions. Isaac Zico was the top receiver, bringing in 21 touchdowns and amassing 945 yards on 80 catches. Jimmie Robinson added 959 rushing yards and 28 scores. The team was 9-3 entering the final three weeks of the regular season and lost three consecutive games on the road. Sioux Falls needed a victory for a home playoff game, and got it with just eleven seconds left in the game to upend the Pirates 62-59. The teams would meet again the following week and Sioux Falls again prevailed 42-39 to end the Pirates' postseason. With 12:25 left in the game, Massachusetts had had an 18 point lead.