The 1967 NHL Expansion depended on securing votes from the then current NHL owners; to ensure that Pittsburgh would be selected for expansion, McGregor enlisted Rooney to petition votes from James D. Norris, owner of the Chicago Blackhawks, and his brother Bruce Norris, owner of the Detroit Red Wings.

The effort was successful, and on February 8, 1966, the National Hockey League awarded an expansion team to Pittsburgh for the 1967 – 1968 season. The Penguins paid $2.5 million ($17.5 million today) for their entry and $750,000 ($5.3 million today) more for start-up costs. The Civic Arena’s capacity was then boosted from 10,732 to 12,500 to meet the NHL requirements for expansion. The Pens also paid an indemnification bill to settle with the Detroit Red Wings, who held the rights to the Pittsburgh Hornets. The investor group named McGregor president and chief executive officer, and he represented Pittsburgh on the NHL’s Board of Governors.

The team had the league’s worst record in both the 1983 and 1984 seasons, and with the team suffering financial problems, it again looked as though the Penguins would fold. Mario Lemieux, one of the most highly touted NHL draft picks in history, was due to be drafted in the 1984 NHL Entry Draft. Heading towards the end of the season ahead of the New Jersey Devils, who were placed last, the Penguins made a number of questionable moves that appeared to weaken the team in the short-term. The Penguins posted three six-game winless streaks in the last 21 games of the season and earned the right to draft Lemieux amidst protests from Devils management. Pittsburgh coach Lou Angotti later admitted that a conscious decision was made to finish the season as the team with the worst record, stating in an interview with the Pittsburgh Post-Gazette that a mid-season lunch prompted the plan, in light of the fact that there was a high chance of the franchise folding if Lemieux was not drafted. In particular, Angotti gave the example of a game the Penguins were winning 3–1, at which point general manager Eddie Johnston asked the coach “what are you doing?” in the first intermission of the game that was eventually lost 6–3. The Penguins were still, despite losing ten of their last twelve games, only two games away from losing Lemieux to the Devils. However, Angotti stated that he did not feel comfortable with the plan, even though it worked and saved the franchise. Other teams offered substantial trade packages for the draft choice, but the Penguins kept the pick and drafted Lemieux first overall.

The 1991 Stanley Cup Playoffs for the National Hockey League (NHL) championship began on April 3, 1991 following the 1990 – 1991 regular season. The sixteen teams that qualified, from the top four teams of the four divisions, played best-of-seven series with re-seeding after the division finals. The Conference Champions played a best-of-seven series for the Stanley Cup.

The 1992 Stanley Cup playoffs, the championship of the National Hockey League (NHL) began on April 18, after the conclusion of the 1991 – 1992 NHL season. It was the 100th anniversary of the first awarding of the Stanley Cup, and it was won by the Pittsburgh Penguins, defeating the Chicago Blackhawks.

The Penguins were simultaneously in the midst of a battle for their survival. Their free spending ways in the early 1990s came with a price; at one point they owed over $90 million to various creditors. Owners Howard Baldwin and Morris Belzberg who bought the Penguins after their first Cup win asked the players to defer their salaries to help pay the bills. When the deferred salaries finally came due, combined with other financial pressures, the Penguins were forced to file for Chapter 11 bankruptcy in November 1998. For much of the 1998 – 1999 season, it looked like the Penguins would either move or fold.

At this point, Lemieux stepped in with an unusual proposal to buy the team out of bankruptcy. By this time, the Penguins owed him $32.5 million in deferred salary, making him the team’s largest creditor. He proposed to convert enough of this money into equity to give him controlling interest. He also promised to keep the team in Pittsburgh. The league and the court agreed, and Lemieux, with help from supermarket tycoon Ronald Burkle, assumed control on September 3, 1999 thus saving the franchise for the second time.

Entering the 2005 NHL Entry Draft, Crosby was listed first overall in the NHL Central Scouting Bureau and International Scouting Services’ respective rankings of prospects. He had also won the Mike Bossy Trophy as the QMJHL’s best prospect. Crosby went on to be selected first overall in the draft by the Pittsburgh Penguins on July 30, 2005. Due to the labour stoppage that suspended the entire 2004 – 2005 NHL season, positioning for the 2005 draft was conducted via a weighted lottery based on each team’s playoff appearances and draft lottery victories in the last four years. This lottery system led to the draft being popularly referred to as the Sidney Crosby Lottery or the Sidney Crosby Sweepstakes.

Crosby made his NHL debut on October 5, 2005 against the New Jersey Devils, and registered an assist on the team’s first goal of the season, scored by Mark Recchi in a 5–1 loss. He scored his first NHL goal in the Penguins’ home opener on October 8 against goaltender Hannu Toivonen of the Boston Bruins. Despite also having registered two assists for a three-point night, the Penguins were defeated 7–6 in overtime. Crosby began his rookie season playing alongside Hall of Famer Mario Lemieux. Unfortunately, Lemieux was forced to retire due to an irregular heartbeat after having played just 26 games of the season.

The 2009 Stanley Cup Final was the best-of-seven NHL championship series of the 2009 Stanley Cup playoffs contested between the Eastern Conference champion Pittsburgh Penguins and the Western Conference champion Detroit Red Wings. It was Detroit’s 24th appearance in the Finals and Pittsburgh’s fourth appearance in the Finals. This was a rematch of the 2008 Finals where Detroit had defeated Pittsburgh in six games. This time Pittsburgh defeated Detroit four games to three to win their third Stanley Cup in franchise history. Pittsburgh’s Evgeni Malkin would win the Conn Smythe Trophy as the Most Valuable Player of the 2009 playoffs, becoming the first Russian-born player to win the trophy.

The 2016 Stanley Cup Finals was the championship series of the National Hockey League (NHL)’s 2015 – 2016 season, and the culmination of the 2016 Stanley Cup playoffs. This was the 123rd year of the Stanley Cup’s presentation. The Eastern Conference champion Pittsburgh Penguins defeated the Western Conference champion San Jose Sharks four games to two to win their fourth championship in franchise history (all of them on the road). The Penguins had home ice advantage in the series, being the club with the better regular season record. The series began on May 30, 2016 and concluded on June 12, 2016. This was the first Stanley Cup Final since 2007 to feature a team making their first appearance in the Finals in their club history.

The 2017 Stanley Cup Finals was the championship series of the National Hockey League’s (NHL) 2016–17 season, and the culmination of the 2017 Stanley Cup playoffs. The Eastern Conference champion and defending Stanley Cup champion Pittsburgh Penguins defeated the Western Conference champion Nashville Predators, four games to two. Penguins captain Sidney Crosby was awarded the Conn Smythe Trophy as most valuable player of the playoffs for the second consecutive year.

The Penguins had home ice advantage in the series due to their better regular season record. The series began on May 29 and concluded on June 11. The Penguins made their second consecutive Finals appearance, marking the third time in their history they had done this, following their appearances in 1991–1992 and 2008–2009. This was the first final since the latter year, which was a rematch between the Penguins and Detroit Red Wings, that any team appeared in consecutive Finals. The Penguins also became the first team since the Red Wings (in 1997 and 1998) to win consecutive Stanley Cups.

The Predators made their debut in the Finals. This was the second consecutive season in which a Western Conference team made their first appearance in the Finals; the San Jose Sharks made their Finals debut the year prior. This was the first time in NHL history that two United States–born head coaches faced off against each other in the Stanley Cup Finals.

The series saw the first two games won by the Penguins, with the Predators coming back winning two games at home and tying the series at two games apiece. However, Penguins goaltender Matt Murray did not allow a goal for the rest of the series, allowing Pittsburgh to win games five and six by 6-0 and 2-0 scores. Pittsburgh coach Mike Sullivan became the third coach in NHL history to win a Stanley Cup in his first two seasons as a coach with his team, joining Pete Green of the Ottawa Senators (in 1920 and 1921) and Toe Blake of the Montreal Canadiens (in 1956 and 1957). This was the first final since 1983 wherein no game was decided by one goal.