The last time was in 1979.
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The once proud Pirates franchise has won the World Series 5 times, the last time in 1979. The last time the Pirates were in the postseason was a 3 year stretch from 1990-1992 where they lost the NLCS in all three years. They have not had a winning season for 17 years.
The last time the cubs were in the world series was 1945. the last time they won was 1907-1908
The Pirates have won 5 World Series. 1909 against the Detroit Tigers 1925 against the Washington Nationals 1960 against the New York Yankees 1971 against the Baltimore Orioles 1979 against the Baltimore Orioles
Anaheim Angels 2002
The San Francisco Giants won the 2010 World Series, defeating the Texas Rangers four games to one.