The Pilots moniker derives from the
Peninsula Pilots (1963–1992), who were a member of the
minor league baseball Class A
Carolina League, who also played at War Memorial Stadium. The Pilots have played in five Petit Cup Finals in their Coastal Plain League existence. They made it to back-to-back Petitt Cup Finals in 2006 and 2007, losing both times to the
High Point-Thomasville HiToms, 6–1 and 4–3 respectively. The Pilots returned to the final in 2009 after winning the North Division where they faced the
Forest City Owls and lost in two games. In 2013 and 2014, Peninsula broke through and won back-to-back titles, winning 2–0 and 2–1 over
Columbia and
Florence respectively. The Pilots set a team record for wins in 2014 when they won the second half East title and the top overall seed in the East. The Pilots are tied for the second most league titles in CPL history with the
Edenton Steamers,
Outer Banks Daredevils,
Wilmington Sharks, and
Forest City Owls, all of whom, including Peninsula, won their titles in consecutive years. The record is three, which is held by the
High Point-Thomasville HiToms, who won three straight. Hank Morgan is the winningest coach in
Coastal Plain League history, with 378 wins as of the end of the 2019 CPL season. Morgan broke the previous record of 289 wins, held by former
Fayetteville SwampDogs manager Darrell Handelsman, on Saturday, July 25, 2015. ==Yearly records==