Last time players won NHL awards, Stanley Cup in same season

Ryan O’Reilly won his only Stanley Cup championship with the St. Louis Blues in 2019. During the playoffs, he scored 23 points in 26 games to win the Conn Smythe Trophy after finishing the regular season as the League’s best defensive forward, winning the Frank J. Selke Trophy. O’Reilly was runner-up for the Lady Byng Trophy and finished 11th in Hart Trophy voting that in 2018-19.

Alex Ovechkin is a nine-time Maurice “Rocket” Richard Trophy winner, but as a one-time Stanley Cup champion, his successes only overlapped once, in 2017-18. That season, he led the NHL with 49 goals, was named to the League’s 100 Greatest Players List, and earned the Conn Smythe with 27 points in 24 playoff games, leading the Capitals to their first Stanley Cup championship.

Jonathan Toews won three Stanley Cup titles and three NHL awards during his 15-season career. One of those trophies was the Mark Messier Leadership Award, which he won in 2015, the last time he won the Stanley Cup. The NHL player receives the award “in recognition of his commitment and service to charities in his community.”

Jonathan Quick has won the William M. Jennings Trophy twice during his career. The trophy goes to the goaltender(s) who surrender the fewest goals during the regular season. After winning the Stanley Cup in 2012 and the Conn Smythe Trophy, he helped the Los Angeles Kings to their second title in 2014, winning the Jennings Trophy with 100 goals against in 49 games during the 2013-14 campaign.

Although the winning fanbase of the Presidents’ Trophy would never want to talk about it, there appears to be a curse associated with being the top regular-season team in the NHL. Since 1986, only eight teams have won the Presidents’ Trophy and the Stanley Cup in the same season. The Chicago Blackhawks were the last team to do so in 2013, with a 36-7-5 record in the shortened 48-game season.

Tim Thomas had a season to remember in 2010-11. Not only did he lead the Boston Bruins to their first Stanley Cup in 39 years with a Conn Smythe Trophy-winning performance as playoffs MVP, but he was also voted the best goalie in the regular season. In 57 games, Thomas was 35-11-9 with a 2.00 goals-against average and a .938 save percentage. He put up even better numbers in the playoffs, at 16-9 with a .940 save percentage and 1.98 GAA with four shutouts, including Game 7 of the Final against the Vancouver Canucks.

Evgeni Malkin is a three-time Stanley Cup champeion and two-time Art Ross Trophy winner. In his third season (2008-09), he helped the Pittsburgh Penguins back to their second consecutive Stanley Cup Final, leading the NHL in scoring with 113 points in 82 games. Malkin was the runner-up for the Hart Trophy and earned the Conn Smythe Trophy as playoff MVP with 36 points in 24 games.

Pavel Datsyuk won eight awards in his Hall of Fame career, capturing the Lady Byng Trophy on three occasions, including in 2008, the same season he won his second Stanley Cup title. In 2007-08, he also won the Frank J. Selke Trophy and finished ninth in Hart Trophy voting, leading the NHL with a plus-41 rating. In 82 games, Datsyuk scored 97 points and had just 20 penalty minutes.

During his fourth season as coach of the Tampa Bay Lightning, John Tortorella led them to the first Stanley Cup championship in franchise history. In the regular season, the Lighting were the second-best team in the NHL, with a record of 46-22-8-6 and 106 points, and Tortorella won the Jack Adams Award as coach of the year, the first of two times he would win this award.

Current Montreal Canadiens coach Martin St. Louis is the last player to win the Hart Trophy and Ted Lindsay Award in the same season as the Stanley Cup. In 82 games, he recorded 94 points and 56 assists while scoring eight shorthanded goals and finishing 2003-04 at plus-35 to lead the NHL in each category.

In 2004, St. Louis’s exceptional performance saw him become only the fourth player since 1969 to win the scoring title with less than 100 points. Despite this, his statistics were not the deciding factor for the voters, giving him 97 first-place votes for the Hart Trophy. The NHLPA also recognized his impact, voting him the League MVP with the Lester B. Pearson Award. At the end of the season, he was rightfully awarded first-team all-star honors.

New Jersey Devils defenseman Ken Daneyko won three Stanley Cup championships during his 20-year career, but only one award, the Bill Masterton Trophy in 2000. Given annually to the player who best exemplifies the qualities of perseverance, sportsmanship, and dedication to ice hockey, Daneyko overcame alcoholism to continue his NHL career.

Scott Gomez is the last Rookie of the Year winner to also capture the Stanley Cup in the same season, achieving the feat in 2000. Just 20 years old at the time, Gomez had 70 points in 82 games. On top of earning All-Rookie honors, the native of Anchorage, Alaska, had 10 points in 23 playoff games as the Devils won their second title in five seasons.