Never. The Pirates won their last World Series 11 years before the Penguins won their first Stanley Cup.
The Penguins made the playoffs in 1970 and 1979, the most recent years the Pirates won, but the Pens failed to win the Cup.
The Pirates won the NL East and won a playoff berth in 1990, 1991, and 1992, the years the Pens won back to back Stanley Cups.
Hockey wasn't that big during the 70s, when it was the "City of Champions". More people were paying attention to the Pitt Panthers NCAA Football team, which in 1976 claimed a National Championship after an undefeated season. They were also Conference champions in 1979.
The Pittsburgh Steelers won Super Bowls in 1974, 1975, 1978, and 1979. The Pirates took the NL East and won a playoff berth in 1974, 1975, and 1979.
In 1980 after both the Steelers and Pirates won championships the previous year
Pittsburgh the steelers and the penguins
Pittsburgh Steelers (NFL) and Pittsburgh Penguins (NHL) in 2008-09
After the 1939 season.
A Steeler was someone who worked in the steel mills. Pittsburgh is famous for their steel production and terrible sports teams (Pittsburgh Power- AFL, Pittsburgh Steelers, Pittsburgh Penguins, Pittsburgh Pirates.) They also are robbers which is weird because they can never "steel" a win. They lose to the Ravens every year.
the Pittsburgh Penguins
1983-84
19200000000
Mario scored 199 points one year
This would be 2009.
This year, both the Pittsburgh Steelers (NFL) and the Pittsburgh Penguins (NHL) won their championships. It was the first time both an NFL and an NHL team won from the same city.
1992