Manny Fernandez
Jeffrey made his NHL debut with the Penguins on December 26, 2008. He recorded his first point on December 30 and his first goal on January 1, 2009, both against goaltender Manny Fernandez of the Boston Bruins. He was called as spare for 2009 playoffs. Pittsburgh gave him a Stanley Cup ring, and included him on the team picture. Jeffrey however did not qualify to be included on the Stanley Cup.