The Pittsburgh Penguins have won five Stanley Cups.
Their championships came in 1991, 1992, 2009, 2016 and 2017. The first two arrived during the Mario Lemieux era, when Pittsburgh defeated the Minnesota North Stars and Chicago Blackhawks in consecutive Finals.
The Penguins returned to the top in 2009 against the Detroit Red Wings, then became the first team since the 1997–98 Detroit Red Wings to win back-to-back championships when they repeated in 2016 and 2017. Sidney Crosby captained those latter three championship teams and won the Conn Smythe Trophy in 2016.
Pittsburgh entered the NHL in the 1967 expansion. The franchise has appeared in six Stanley Cup Finals, losing only the 2008 Final to Detroit. That makes five wins, not six: the sixth Final appearance was a defeat.