They have won the Stanley Cup five times (1991, 1992, 2009, 2016, & 2017) as of 2017.
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The record for the Pittsburgh Penguins overall for the 2013-2014 season was 51-24-7. The first game of the next season is on September 22, 2014.
Three. 1990-91 season, 1991-92 season, and 2008-09 season.
There is a list of all the Stanley Cup winners here
proicehockey.about.com/od/stanleycupbunker/a/stanley_cuplist.htm