In 2002, the O'Leary Eagles won the Don Johnson Cup as Maritime Junior B champions. Nine years later, in 2011, the Kensington Vipers repeated the act as Maritime champions, following up their success again in 2013 and 2023 respectively.
Following the 2021-22, the league lost both the Western Red Wings and Eastern Maniacs but added the Kings County Rivermen. With only 3 remaining teams, the league negotiated to play regular season games with the New Brunswick Junior B Hockey League (NBJHL), with PEI holding their own playoff series.
For the 2023-24 season, the Sherwood Metros and Kings County Rivermen merged and, along with Kensington, will once again compete in the NBJHL to determine the PEI representative for the Don Johnson Memorial Cup.