2009 – 10 Boston Bruins season The 2009 – 10 Boston Bruins season is the Bruins ' 85th season in the National Hockey League ( NHL ) . Their regular season began with a nationally - televised home game against the Washington Capitals on October 1 , 2009 , and ended with a road game against the same Capitals team on April 11 , 2010 . The Bruins failed to defend their regular - season division and conference titles from the 2008 - 09 season . Off - season . At the Entry Draft , the Bruins chose Jordan Caron with their first - round pick , 25th over - all . The NHL announced on July 15 , 2009 , that the Bruins would face the Philadelphia Flyers in the 2010 NHL Winter Classic on New Year ' s Day at Fenway Park . Due to salary cap constraints and free agent movement , General Manager Peter Chiarelli made substantial changes to the Bruins ' lineup in the offseason . Most notable was the trade of leading goalscorer Phil Kessel , who declined contract offers and was traded to the Toronto Maple Leafs for three draft picks on September 18 . Other departures included longtime Bruin winger P . J . Axelsson , center Stephane Yelle , defensemen Shane Hnidy and Steve Montador , and goaltender Manny Fernandez . These veteran players were considered expendable due to competition from younger , lower - paid players in the Bruins organization . Chiarelli entered the 2009 offseason with the goal of acquiring an offensive - minded defenseman , in part due to Boston ' s weakness in that area during the previous playoffs . On July 24 , defenseman Derek Morris signed a one - year contract with the team . Gritty forward Steve Begin was also signed to provide forward depth . In goal , Fernandez was replaced with rookie Tuukka Rask , who had spent several seasons being developed in the AHL . Regular season . The Bruins were slow to gain traction with their retooled roster , alternating wins and losses in the early weeks of the season . Chiarelli quickly dealt popular winger Chuck Kobasew to Minnesota for gritty Daniel Paille , a move that was interpreted as a sign of dissatisfaction with the team ' s productivity . In particular , the team struggled offensively in Kessel ' s absence . Having nearly finished first in scoring the previous season , the Bruins lingered near the bottom of the league in goal production . However , they were able to stay competitive due to their exceptional defense and strong goaltending tandem . While defending Vezina Trophy winner Tim Thomas was recovering from an early injury , rookie netminder Tuukka Rask emerged as a potential Calder Trophy candidate . A four - game winning streak in November set the Bruins back on course , and a 5 - 1 - 0 home record in December got them back into the divisional race by Christmas . Perhaps the most memorable game of the season was the Winter Classic , which the Bruins hosted at Fenway Park in Boston . Despite trailing for most of the game , they rallied in the final moments and won in overtime before a large national audience . After the game , Thomas was announced as a member of the United States men ' s hockey team , joining five teammates ( Bergeron , Chara , Sturm , Krejci , and Satan ) who would represent various countries in Vancouver . The Bruins went on a long losing streak lasting from Mid - January to just before the Olympic break . In the 81st game of the season the Bruins scored 3 short handed goals in a span of 64 seconds giving the 2009 - 2010 team the nickname " shorty . " The 4 - 2 victory over the hurricanes secured the bruins of a playoff spot . Playoffs . The Bruins clinched a playoff spot for the third consecutive season . Awards and records . Awards . On April 8 , prior to the game against the Buffalo Sabres , the team announced its award winners for the season . Milestones . On December 23 , Claude Julien coached his 200th game for Boston , a 6 – 4 win over Atlanta . Transactions . The Bruins have been involved in the following transactions during the 2009 – 10 season . Draft picks . Boston ' s picks at the 2009 NHL Entry Draft in Montreal , Quebec .