He led the team that year with 163 penalty minutes, just one more minute than Cody McLeod. Unable to agree to a new deal with the Avalanche, Laperrière signed a three-year contract with the Philadelphia Flyers on July 1, 2009. On November 27, 2009, Laperrière was hit with a slapshot in the mouth while killing a penalty at the end of the first period against the Buffalo Sabres. He sat out the second period receiving between 50 and 100 stitches but returned for the third period. He also played the following night against the Atlanta Thrashers. Laperrière lost seven teeth resulting from the incident (two fake and five real). A similar event occurred during the 2010 Stanley Cup playoffs on April 22. Laperrière was hit in the face near the end of a New Jersey power play, resulting in an orbital injury, and a mild concussion. Laperrière was listed as out indefinitely and his return to the playoffs was considered unlikely. However, after missing the Flyers second round series versus the Boston Bruins, he returned for game 4 of the Eastern Conference Finals against the Montreal Canadiens. In the May 2010 edition of The Hockey News, Laperrière was awarded THN's John Ferguson Award for "Toughest Player in the NHL" in the 2009–10 season. Post-playing career NHL retirement During training camp in September 2010, Laperrière experienced symptoms of post-concussion syndrome and nerve damage to his eyes from being hit in the face twice by pucks the previous season. He was then out for the entire 2010–11 season after being put on injured reserve before the season began and then on long-term injured reserve in mid-December to free up salary cap space. Doctors advised Laperrière to retire, although he did not do so at the time. The move was repeated again for the season to free up cap space when Laperrière's symptoms still had not subsided. His number 14 was reissued to rookie Sean Couturier. Despite never playing again after the 2010 Stanley Cup Finals, Laperrière continued to serve the Flyers off the ice as a mentor to younger players in the organization and in other capacities. For that, Laperrière was awarded the 2011 Bill Masterton Trophy for his perseverance in the sport of hockey. Laperrière officially retired June 12, 2012. Philadelphia Flyers On June 29, 2012, Laperrière was named director of player development for the Philadelphia Flyers. The following year, in