The Port Dover Clippers were founded in 1988 as members of the Niagara & District Junior C Hockey League. The Clippers were 1990 and 1991 Niagara East champions and Niagara co-champions. In 1990, the Clippers would fall to the Orangeville Crushers of the Mid-Ontario Junior C Hockey League 4-games-to-1 in the Clarence Schmalz Cup OHA provincial quarter-final. Their western co-champions, the New Hamburg Spirit 83's would fare no better, dropping one of the other quarter-finals in four-straight games to the Great Lakes Junior C Hockey League champion Belle River Canadiens. The next year was more of the same, as Port Dover and New Hamburg were the co-champions, New Hamburg lost the provincial quarter-final to Belle River again (this time in six games), and Port Dover fell to Orangeville again in five.
In 1999, the Clippers took leave of the Niagara District league. Clippers changed their name to the Port Dover Sailors and applied for membership in the Ontario Hockey Association Junior Development League.
From 2011 until 2013 the team was known as the Norfolk Rebels and split time between Port Dover and Waterford, Ontario.
In 2013, the team was renamed the Port Dover Sailors.
The playoffs for the 2019-20 season were cancelled due to the COVID-19 pandemic, leading to the team not being able to play a single game.
In 2022-23 The Sailors created a record breaking season led by Captain Benjamin Mason. Assistant Captain Nick D’Agostino set a new record for Points in a Season and won Most Sportsmanlike Player. Goaltender Finn Wilson won Rookie of the Year. Also Head Coach Mike Walker won Coach of the Year.
The team went into playoffs as the 3rd ranked team. Completing their first franchise sweep over the Dunnville Mudcats 4-0, and also won there first 2nd round series game (Jr.C) dating back to the 1990-91 season.
