The Penguins have won three Stanley Cups ('90-91, '91-'92, '08-'09). The Flyers have won two Stanley Cups ('73-'74 and '74-'75). The Penguins have won three Stanley Cups ('90-91, '91-'92, '08-'09). The Flyers have won two Stanley Cups ('73-'74 and '74-'75). The Penguins have won three Stanley Cups ('90-91, '91-'92, '08-'09).