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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.

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Q: When did the Pittsburgh Penguins and Pittsburgh Pirates win in the same year?
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