They lost to the Montreal Canadiens in 2010 before allowing a 3-1 series lead to slip away against the Tampa Bay Lightning a year later. In 2012, the Penguins lost a turbulent series to the Philadelphia Flyers in six games before being swept by the Bruins in the 2013 Eastern Conference Final.
Pittsburgh allowed the New York Rangers to come back from a 3-1 series deficit in 2014 and was eliminated by New York again in 2015, when the Penguins lost a first-round series in five games.
The fans weren't expecting that level of adversity. Those moments have led to Wednesday, when the Penguins and their fans will release that frustration.
Pittsburgh's celebrations have evolved from a park gathering in 1991 and a rally at Three Rivers Stadium the following year. Each has looked significantly different but shared the same flavor.
Former Penguins forward Phil Bourque, now a radio analyst on 105.9 FM in Pittsburgh, has helped bridge the gap between each championship.
In 1991, he asked a roaring crowd, "What do you say we take [the Stanley Cup] out on the river and party all summer?" A year later, he punctuated a poem by saying, "Let's take this Cup to the river for some more fun because one time wasn't enough. Enjoy it, Pittsburgh, we're No. 1."
After the 2009 run, Bourque took to the microphone atop the stage at Stanwix Street and reiterated his hope for a summer-long river party.
When Wednesday arrives in Pittsburgh, history shows only one thing can be expected: Bourque will want to take the Cup out on the river and party all summer.