Armstrong had three overtime goals for the Penguins in the 2006–07 season, beating Kari Lehtonen of the Atlanta Thrashers, Ed Belfour of the Florida Panthers and Henrik Lundqvist of the New York Rangers. The Penguins and Armstrong avoided an arbitration hearing in the 2006–07 off-season by re-signing him to two-year, $2.2 million contract. Armstrong became very close friends with teammate Sidney Crosby while playing for the Penguins. On January 1, 2008, Armstrong scored the first ever outdoor Winter Classic goal in the inaugural event.