Advancing to the South Sectional Finals, Rockland knocked off their longtime rival, the Norwell Clippers, in dramatic fashion to move onto the State Semi-Finals at the then Fleet Center.

The Bulldogs upset Lynn Tech in the Semi-Finals, and, led by Captain Joe Coppens' 31 points, beat New Leadership High School, 63-60, in the State Championship game.

Between 2007 and 2018, the Bulldogs only missed qualification for the State Tournament in the 2008–2009 season, and multiple times made deep runs, including Sweet Sixteen appearances in 2013 and 2016.

Since 2020, the team has struggled to maintain the high expectations that have been fostered over the last two decades of success; in the 2021–22 season, the program failed to qualify for the tournament with a record of 7–13.

The Rockland hockey team made a run to the South Sectional Finals in 2011-12, posting a regular season record of 14–5–1 while knocking off Blue Hills Regional and Somerset-Berkley in the first two round respectively.

Serious underdogs, Rockland upset Medfield, 6–2, en route to the finals, where the scrappy Bulldogs fell to Medway High, 4–1.