The Pirates were affiliated with the Washington Capitals (1993–2005), the Anaheim Ducks (2005–2008), the Buffalo Sabres (2008–2011), Arizona Coyotes (2011–2015), and the Florida Panthers (2015–2016).

Tom Ebright, owner of the Baltimore Skipjacks, had a daughter who was an intern at the East Coast Hockey League's Nashville Knights.

[4] The Pirates filled the void made by the Maine Mariners who had departed to become the Providence Bruins a year earlier.

On August 4, 1993, forward Eric Fenton was signed to a professional contract to become the very first member of the Portland Pirates team.

The Pirates first season proved to be their most successful as they won the Calder Cup with a 43–27–10 record and was third overall in attendance with an average of 5,872 fans.

In the 1995–96 season they again reached the Calder Cup Finals, despite a sub-par record of 32–34–10, but lost to the Rochester Americans.

In 2005, the Pirates announced a five-year lease extension at the Cross Insurance Arena, ending speculation that the team might relocate.

On June 10, 2008, the Pirates and the Buffalo Sabres announced that they had reached a new affiliation agreement, ending several months of speculation.

On June 27, 2011, the Phoenix Coyotes announced that the franchise had entered into a five-year player development contract with the Pirates.

[12] During the 2012–13 season, the Pirates played six games at the Androscoggin Bank Colisee in Lewiston, Maine in preparation of renovations at the Cross Insurance Arena.

[13] On May 7, 2014, they announced a one-year extension of the affiliation agreement and a small increase in ticket prices as part of the changes the team was doing to rebuild confidence with the community.

The Chairman of the Cross Insurance Arena Board of Trustees criticized the Pirates for demanding more of a "subsidy" for themselves and stated their desired lease agreement would cost county taxpayers money.

[17] On October 24, 2013, it was announced that the team had taken out an option on city-owned land in Saco for possibly building a $40 million arena with 5,000 seats as a new home.

Owner Ron Cain also revealed that he had explored the possibility of moving the team to Glens Falls, New York to replace the departing Adirondack Phantoms, going so far as to send CEO Brian Petrovek to Glens Falls for discussions, but that he wanted the Pirates to remain in Maine too much to do so.

[28] By March 8, the arena owners had narrowed their choices to the proposals submitted by Spectra and National Sports Services, with both groups having been involved with managing ECHL teams in their past.

[29] In June 2017, Comcast Spectacor, the operators of the Cross Insurance Arena and the NHL's Philadelphia Flyers, purchased the franchise rights of the recently dormant Alaska Aces of the ECHL.

However a banner still hangs in the rafters in tribute to the 5 Maine Mariners who had their number retired before moving to Providence.