In the 51 seasons since the Pittsburgh Penguins joined the NHL in 1967, they have won the Stanley Cup championships five times. During all five postseasons, Pittsburgh played significant games on May 25 or May 26.

On May 25, 1991, the Penguins won their first Stanley Cup championship. They had ended the regular season with 88 points, which put them first in the Patrick Division but seventh in the NHL. During playoffs, they knocked out the New Jersey Devils (4-3), the Washington Capitals (4-1), and the Boston Bruins (4-2) to advance to the finals against the Minnesota North Stars. For the Cup, Pittsburgh won the finals (4-2) with an 8-0 shutout at the Met Center. With 39 saves, Tom Barrasso had earned his first NHL playoff shutout.

The defending champions returned to the Stanley Cup finals in 1992. They had again finished seventh in the NHL (but third in the Patrick Division) with 87 points. This time, they eliminated the Capitals (4-3) and then the New York Rangers (4-2). The Bruins again were their victims in the conference finals during Pittsburgh’s sweep. The finals began on May 26 at Pittsburgh’s Civic Arena. Although the Chicago Blackhawks scored three unanswered goals to start the first period, the Penguins battled back. With five minutes remaining, Jaromir Jagr tied the game at 4-4, and then, with mere seconds to spare, Mario Lemieux potted the game-winner during a power play. Chicago’s record streak of 11 playoff wins ended, and Pittsburgh prevented them from winning any more. In the midst of the sweep, for Game 3 on May 30, Barrasso would have his only other playoff shutout.

In both postseasons, center Mario Lemieux led the scoring and received the Conn Smythe Trophy as MVP. Having scored 16 goals in each, he also had 28 assists in 1991 and 18 assists in 1992. He had one of those goals and three assists at the May 25th game in 1991. His two goals helped tie and then win the game on May 26, 1992.

Pittsburgh always seemed to make it to the championships in back-to-back years. In both 2008 and 2009, the Penguins played the Detroit Red Wings in the finals. For the two seasons, the Pennsylvanian team placed first (with 102 points) and second (with 99 points), respectively, in the Atlantic Division. The May 26th game went very differently, as did the result of the finals. In 2008, the Penguins lost Game 2 of the finals with a 3-0 shutout and went on to lose the series 4-2. On May 26, 2009, Pittsburgh won Game 4 of the Eastern Conference finals 4-1. Having swept the Carolina Hurricanes, they advanced to the finals, which they won 4-3.

The Penguins’ most recent back-to-back Stanley Cup championships occurred in 2016 and 2017. With 104 points and 111 points, respectively, they placed second in the Metropolitan Division both seasons. They mostly faced different opponents throughout the two postseasons. To make it to the finals in 2016, Pittsburgh defeated the New York Rangers (4-1), the Washington Capitals (4-2), and the Tampa Bay Lightning (4-3). The following year, they passed the Columbus Blue Jackets (4-1), the Washington Capitals (4-3), and the Ottawa Senators (4-3).

On May 26, 2016 and May 25, 2017, the Penguins played Game 7 of the conference finals. Both games took place at Pittsburgh, the former at the CONSOL Energy Center and the latter at PPG Paints Arena. The Penguins scored first and then alternated scoring with their opponents until they came out on top. In 2016, Pittsburgh rookie Bryan Rust scored the first and third goals of the game, all within the second period, to give his team a 2-1 victory. Having vanquished Tampa Bay, the Penguins went on to defeat the San Jose Sharks (4-2) in the finals. In 2017, Pittsburgh and Ottawa each scored one goal in the second and third periods. Ending regulation tied 2-2, they went through one overtime session and 5:09 into the second. At that time, Pittsburgh’s Chris Kunitz sunk his first goal of the playoffs to advance his teams to the finals. There, the Penguins defeated the Nashville Predators 4-2.

Throughout the latest four postseasons in which the Penguins made it to the finals, Evgeni Malkin and Sidney Crosby have vied for the top scorer. In 2008, Crosby topped with 27 points while Malkin came in third with 22. The following year, Malkin had 36 points and Crosby trailed with 31. Come 2016, Crosby placed second with 19 while Malkin followed with 18 points. Finally, in 2017, Malkin led the pack with 28 points while Crosby had one less. Malkin received the Conn Smythe Trophy in 2009, and Crosby took home the award in both 2016 and 2017.

The Penguins have not missed the playoffs since 2007.

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