Screen cap: Youtube

After losing in Round 1 for the fourth consecutive season, it’s not difficult for Washington Capitals fans to feel depressed about their team, especially when their core players are growing long in the tooth. But, to put things in perspective, some teams have had, in many ways, an even more tortured playoffs than the Capitals. 

Toronto Maple Leafs

The Leafs last won the Stanley Cup back in the 1966-67 season, the very last season of the Original Six Era. As the Leafs’ Stanley Cup woes continue, many of the expansion teams added since their last Cup have won the Stanley Cup themselves.

The Leafs have lost in the first round (or a play-in round), six consecutive seasons. This includes losing Game 7 to close-out four out of the last five seasons, including this season when they lost to Tampa Bay in seven games.

The last time the team advanced past the first round was in 2003-04, when they beat the Ottawa Senators, the season immediately before the NHL lockout that resulted in cancelling the 2004-05 season. They have not been back to the Stanley Cup Finals but lost in the Eastern Conference Finals on five occasions.

To put their drought in perspective, they last won the Stanley Cup when Lyndon Johnson was President; they last advanced past the first round before any player currently on the Washington Capitals played in the NHL.

Toronto Maple Leafs History: Hockey Reference

Photo: NHL

Buffalo Sabres

The Buffalo Sabres first joined the NHL for the 1970-71 season and have never won the Stanley Cup. They made it to the Stanley Cup Finals twice, losing to the Philadelphia Flyers in 1974-75 and the Dallas Stars in 1988-89.

The last time the Sabres advanced past the first round was in 2006-07, when they beat the New York Islanders to advance to the Eastern Conference Finals.

The last time they made the playoffs was in the 2010-11 season, after finishing in second place in the Northeast Division. In 2015, they drafted Jack Eichel with the second overall pick, who they expected to be their franchise player. Eichel is now gone and they are starting yet another rebuild.

Buffalo Sabres History: Hockey Reference

Vancouver Canucks

The Vancouver Canucks first joined the NHL for the 1970-71 season and have never won the Stanley Cup. They made it to the Stanley Cup Finals three times, losing to the New York Islanders in 1981-82, the New York Rangers in 1993-94, and the Boston Bruins in 2010-11.

The Canucks had a very strong team from 2000-01 through 2014-15, missing the playoffs just three times in the stretch. They won the Presidents’ Trophy in 2010-11 and 2011-12, losing the Stanley Cup in the former season, but getting eliminated in the first round in the latter. They have recently been in a rebuilding process and made the playoffs just once in the last eight seasons, the 2019-20 season.

Vancouver Canucks History: Hockey Reference

Ottawa Senators

The Ottawa Senators first joined the NHL for the 1992-93 season, have never won the Stanley Cup and have made it to the Stanley Cup Finals just one time, losing to the Anaheim Ducks in 2006-07. They have missed the postseason during each of the last six seasons, last making the playoffs in 2016-17, when they advanced to the Eastern Conference Finals.

Ottawa Senators History: Hockey Reference

San Jose Sharks

The San Jose Sharks first joined the NHL for the 1991-92 season, have never won the Stanley Cup and made it to the Stanley Cup Finals just one time, losing to the Pittsburgh Penguins in 2016-17.

The Sharks have missed the playoffs the last three seasons. Prior to that, they made the playoffs nearly every year from 2003-04 through 2018-19, except one season, and nearly every year from 1999-2000, missing just twice. Their key players from their long run of contention, Patrick Marleau, Joe Thornton, and Joe Pavelski, have all left the Sharks and gone elsewhere.

San Jose Sharks History: Hockey Reference

Philadelphia Flyers

The Flyers won the Stanley Cup back in 1974-75 for their second consecutive championship. They have advanced to the Stanley Cup Finals six more times since then: 1975–76, 1979–80, 1984–85, 1986–87, 1996–97, and 2009–10.

The last time they won a playoff round was during the 2019-20 playoffs. Their other playoff appearances since 2012-13 were three first-round losses.

Philadelphia Flyers History: Hockey Reference

Arizona Coyotes

The Arizona Coyotes first joined the NHL for the 1979-80 season when they were known as the Winnipeg Jets. They have not only never won the Stanley Cup but have never even made it to the Stanley Cup Finals.

The Coyotes advanced to the Conference Finals just once during their history, the 2011-12 season where they then lost to the Los Angeles Kings. They have made the playoffs just once since 2012-13 and that was in 2019-20.  The Coyotes will start playing in the Arizona State University arena in 2022-23, an arena with a capacity of just 5000 fans, until a new arena is built for them.

Arizona Coyotes History: Hockey Reference

Winnipeg Jets

The Winnipeg Jets first joined the NHL for the 1999-2000 season when they were known as the Atlanta Thrashers. They have not only never won the Stanley Cup but have never made it to the Stanley Cup Finals. They have advanced to the Conference Finals just once during their history, 2017-18 when they lost to the Las Vegas Golden Knights.

Winnipeg Jets History: Hockey Reference

By Diane Doyle