In the 2005–06 season, Cleary established himself as a dependable role player as a defensive forward. In the 2006–07 season, given an expanded role with the Wings, Cleary scored a career high 20 goals in 71 games. During the 2006–07 NHL playoff quarterfinals against Calgary, Cleary successfully converted a penalty shot while shorthanded; this was the first time it had been done in Detroit during the playoffs. In the 2007–08 season, Cleary repeated the accomplishment of scoring 20 goals in the regular season. On February 9, 2008, Cleary suffered a broken jaw which forced him to miss 19 games. On March 11, 2008, Cleary signed a five-year contract extension with the Detroit Red Wings, worth $14 million. On June 4, 2008, Cleary won the Stanley Cup with the Detroit Red Wings as they beat the Pittsburgh Penguins four games to two in the Stanley Cup Final, becoming the first Newfoundlander to do so. On June 30, 2008, Cleary brought the Stanley Cup home to Newfoundland. A packed lobby welcomed Cleary at the St. John's International Airport. Later that day, Cleary brought the Cup to the Janeway Children's Hospital. On July 1, 2008, Cleary brought the Stanley Cup back to his hometown of Harbour Grace, Newfoundland for a Canada Day celebration that included a parade and a concert. The event attracted an estimated 27,000 people. The event also attracted an estimated 103 individual media accreditations with media from across Canada and the United States landing in Harbour Grace to cover Dan Cleary's story. The Newfoundland bluegrass/folk band Greeley's Reel recorded a "hockey anthem" version of their song "Come In" about Cleary after the win. The refrain specifically highlights the celebration that would occur "when Danny Cleary brings the Stanley Cup to Newfoundland." In addition to receiving extensive local radio airplay, the song appeared on CBC Television and a Fox Sports Detroit special. In the 2009 Stanley Cup playoffs on May 14, 2009, Cleary scored the tie breaking, Western Conference semi-final series winning goal for the Detroit Red Wings against the Anaheim Ducks with three minutes left in game seven. With the win the Red Wings moved on to face the Chicago Blackhawks in the Western Conference Final. Cleary scored five goals against his former team in a 4-1 series win clinching the Western Conference title before succumbing to the Pittsburgh Penguins in seven games in a rematch of the previous Stanley Cup final. In 2009, Cleary founded the Danny Cleary Hockey School in his native province of Newfoundland.