Top 10 worst moments in Ottawa Senators franchise history

When a team has won no Stanley Cups in franchise history, it's safe to say that there has been a lot of painful moments that have happened to a franchise. The Ottawa Senators are one of the 10 teams in the NHL that haven't won a Stanley Cup.

The Senators began their existence in the 1992-93 season. For over 30 years, the franchise has had a lot of painful moments. However, some might be worse than others.

Top 10 worst moments in Ottawa Senators franchise history

Most of these moments have made Senators fans cringe and caused a lot of pain. From heartbreaking losses, to emotional trades and more, these are moments that Senator fans can remember where they were when they happened.

10. Eastern Conference title defense swept away

The Senators entered the 2007-08 season looking to defend their Eastern Conference title with their big three of Jason Spezza, Daniel Alfredsson and Dany Heatley. The season started off hot with a 16-3-0 record, but the Senators finished as the seventh seed in the Eastern Conference.

Standing in the Senators' way were the Pittsburgh Penguins. In the 2007 playoffs, the Senators defeated the Penguins in five games. With beating the Penguins and having experience from the year before, some thought the Senators had the right opponent for round one again to go back to the Stanley Cup Finals.

Long story short, the 2008 playoffs were a disaster for the Senators. The Penguins easily swept the Senators to put an embarrassing playoff performance to bed, and the Penguins would ride their momentum until they fell to the Detroit Red Wings in the Stanley Cup Finals. 2008 also marked the final time Ottawa's big three would make the playoffs together.

9. Historic bad first season goes down in ugly infamy

In 1991, the NHL would bring hockey back to Ottawa with the expansion Senators, but the Senators would have to wait until the 1992-93 season to begin their existence. 1992 marked the first time that the NHL would be played in Ottawa since the original Senators moved in 1934 to St. Louis, Missouri.

The NHL returning to Ottawa for the first time in 58 years brought excitement for Ottawa citizens, but the excitement quickly turned ugly. In one of the worst seasons by a team in NHL history, the Senators finished with putrid 10-70-4 record. Ottawa's record was good for 24 points overall. Five players on the team had a +/- rating of -40 or worse. In another lopsided stat, the Senators were outscored 395 to 202 during the season.

The head coach of the 1992-93 Senators was Rick Bowness. If someone said 17 years later that Bowness would help lead the Dallas Stars to the 2020 Stanley Cup Finals as interim head coach, most would've said absolutely not. Laurie Boschman served as the Senators captain during the historic bad season in 1992-93, and only recorded 16 points on the season. After the 1992-93 season, Boschman never played an NHL game again.

On a bad team, Norm Maciver would lead the team with 63 points, and also led the team with 46 assists. Sylvain Turgeon led the team with 25 goals, but no other player on the team outside of Maciver recorded over 50 points. Goaltender Peter Sidorkiewicz finished the season with a 8-46-3 record with a 4.46 goals against average. For the Senators to be part of one of the worst seasons in NHL history, it will always be ugly for the franchise.

8. Almost pulling off the 8-seed upset in 2012

The Senators missed the playoffs in 2011 after making it in 2010. In 2012, the team got a big breakthrough from their young stud defenseman Erik Karlsson who would win the 2012 Norris Trophy at 21 years old. Karlsson's role was a key reason the Senators were able to sneak in the 2012 playoffs as an eighth seed. The Senators would be matched up against the heavily favored New York Rangers who finished with 17 more points than the Senators.

Even with the Rangers being a heavy favorite to win the series, it didn't bother the Senators one bit. Three of the first four games of the series were decided by one goal, and both of Ottawa's wins through the first four games were won in overtime.

The Senators sneaked out an impressive 2-0 shutout win in Game 5 to set up a chance to clinch the series and upset the Rangers at home in Game 6. The Senators lost Game 6 by a final of 3-2 to have a Game 7 be played in New York City. Game 7 was another similar result with the Senators losing by one goal for the second consecutive game. The Senators lost Game 7 by a final of 2-1 and were eliminated from the 2012 playoffs.

Five of the seven games in the series would be determined by one goal. For an eighth seed team to lose back-to-back games to lose the series by one goal will sting because upsets in the playoffs are remembered forever.

Had the Senators defeated the Rangers, they would've played the Philadelphia Flyers in the second round. The eventual Eastern Conference champion New Jersey Devils dominated the Flyers in five games in the second round, so the thought of having Ottawa dominate Philadelphia in the playoffs adds insult to injury.

6. Matt Duchene trade backfires immediately

After falling in the 2017 Eastern Conference Finals, it was obvious the Senators were missing a key offensive piece to give an extra boost. One month into the 2017-18 season, the Senators completed a three-team trade with the Colorado Avalanche and Nashville Predators to acquire former 2014 Gold Medal Olympian Matt Duchene.

Duchene had grew frustrated in Colorado and wanted a trade out. When Duchene was traded to Ottawa, he appeared to be the missing piece as Ottawa had a 6-3-5 record at the time of the trade.

Instead, the Duchene trade would set the Senators back. The Senators traded fan favorite Kyle Turris to the Predators. While Turris didn't perform well with the Predators, the key draft pick the Avalanche received in the trade was the Senators' 2019 first-round draft pick. Had the Senators not trade away the draft pick, they could've had the chance to select players from Moritz Seider, Dylan Cozens or Trevor Zegras.

Duchene would be traded by the Senators to the Columbus Blue Jackets before the 2019 trade deadline, and Duchene would help the Blue Jackets win their first playoff series in franchise history in 2019. After Ottawa, Duchene would record a career-high 43 goals and 86 points in the 2021-22 season with the Predators. Today, Duchene is a key player on the Stars roster.

The Avalanche would win the 2022 Stanley Cup after the trade, and the Senators have failed to make the playoffs since the trade.

5. Losing Game 7 to the hated Maple Leafs in 2002

The Senators' arch rival in the NHL are the Toronto Maple Leafs. The Battle of Ontario intensifies more with every game. The two teams have met four times in the playoffs with the result being the same with the Maple Leafs eliminating the Senators, but no playoff series loss was worse against the Maple Leafs than in 2002.

After the Senators defeated the Flyers in the first round of the 2002 playoffs, the Senators had a date with the Maple Leafs in round two. Even without having home ice advantage, the Senators believed they can knock off the Maple Leafs.

The series immediately started in Ottawa's favor when Ottawa won 5-0 in Game 1. The Maple Leafs won a hard fought triple overtime game in Game 2 to even the series. For the next two games in Ottawa, each team won a one-goal game to make the series tied at two going back to Toronto for Game 5.

The Senators put themselves in position to knock off their arch rival in round two after winning Game 5 by a final of 4-2. With the Ottawa crowd buzzing for Game 6, the Senators suffered a heartbreaking 4-3 loss in Game 6, and at one point held an early 2-0 lead. The Senators were shutout 3-0 in Game 7 and were eliminated from playing in the 2002 Eastern Conference Finals against the Carolina Hurricanes.

Losing Game 7 to your arch rival will always be a heartbreaking and painful moment, and 2002 will always live on in the Senators-Maple Leafs rivalry.

4. The captain gets traded

There are trades that are emotional and hurt a franchise and fan base. One trade that did that was the Senators in September 2018.

One month before the 2018-19 season, the Senators traded their then captain Erik Karlsson to the San Jose Sharks. Karlsson served as Senators captain for the past four seasons and the trade was a heart breaker.

Karlsson was a two-time Norris Trophy winner and was arguably the best defensemen in the NHL year in and year out with the Senators. The Senators reached the playoffs five times with Karlsson on the team and were one game away from the 2017 Stanley Cup Finals.

Although the Senators did acquire Josh Norris in the trade, the Senators haven't made the playoffs since the trade, and have been a door mat for years. In the first year of the trade, the Sharks made the 2019 Western Conference Finals, and Karlsson won the 2023 Vezina Trophy with the Sharks after recording a 102-point season.

Karlsson will go down as one of the best players from the 2010s for his incredible talent and accomplishments, but being traded as the captain was emotional for everyone. When considering how the Karlsson trade could've been considered by many as the acceptance of the start of the Senators rebuild, it makes the moment hurt more. If Karlsson was not traded in 2018, the direction of the Senators could've been much different.

3. Stanley Cup Finals defeat in 2007

Entering the 2007 Stanley Cup Playoffs, the Senators were finally looking to get over the hump. The franchise did when they reached the 2007 Stanley Cup Finals. To win the Eastern Conference, the Senators knocked off the 2007 President's Trophy winner Buffalo Sabres.

The Senators were led by their top line of Daniel Alfredsson, Jason Spezza and Dany Heatley. Ray Emery turned into a reliable goaltender during the 2007 playoffs as well. Standing in the Senators' way of hoisting Lord Stanley were the Anaheim Ducks. The Ducks were another team looking to get over the hump after losing in the 2003 Stanley Cup Finals and in the 2006 Western Conference Finals. With both teams looking to win their first Stanley Cup in franchise history, the stage would be set.

Anaheim started the series with protecting home ice in the first two games of the series. Even with losing both games by one goal, the Senators still were confident going home for the next two games behind their rowdy fans. The Senators won Game 3 to get back into the series, but were crushed when the team lost their third one-goal game of the series in Game 4 by a final of 3-2. What fans might remember the most from Game 4 is Alfredsson shooting the puck at Scott Niedermayer with time running down in the second period.

In Game 5, the Senators had their backs against the wall, and Game 5 started rough when the Senators trailed 2-0 after the first period. The Senators cut the lead down to one on two different occasions in the second period, but faced a two-goal deficit again when Francois Beauchemin scored a powerplay goal to give the Ducks a 4-2 lead heading into the second intermission.

The Ducks scored twice in the third period to ice the game and won Game 5 by a final of 6-2 to win the Stanley Cup. The first Stanley Cup Final loss will always be a tough pill to swallow. Since 2007, the Senators have never made it back to the Stanley Cup Finals.

2. Chris Kunitz eliminates Senators in 2017 Eastern Conference Finals

When the Senators began their quest to win the 2017 Stanley Cup Playoffs, not many gave the team a shot to win it all. However, it didn't bother the Senators one bit.

The Senators silenced critics when they advanced to the Eastern Conference Finals for the first time in a decade after eliminating the Rangers on the road in Game 6 in the second round. Standing in the Senators' way to win the East were the defending Stanley Cup champion Penguins. When the Senators made the Stanley Cup Finals 10 years prior, they defeated the Penguins in the playoffs, so the Senators were eager to continue their irony of defeating the Penguins in their quest to reach the Stanley Cup Finals.

After four hard fought games, the series was tied up at two after a Penguins 3-2 win in Game 4. Hope appeared to be gone for the Senators after an embarrassing 7-0 defeat in Game 5, but the Senators responded with a 2-1 win in Game 6. A Game 7 was needed in the Steel City.

The Senators trailed 2-1 past halfway of the third period after a Justin Schultz powerplay goal, but Ryan Dzingel tied the game with 5:19 remaining in the period. Overtime would then be needed to decide who is going to advance to the Stanley Cup Final.

Momentum was on the Senators side with not only scoring late to tie the game, but they had won Game 1 of the series in overtime. After a scoreless first overtime, a second overtime was needed.

Stanley Cup hopes and dreams were dashed when Chris Kunitz fired a shot past Craig Anderson to advance the Penguins for the Stanley Cup Final for the second consecutive season. The Penguins went on to defeat the Nashville Predators in the 2017 Stanley Cup Finals, so Senator fans were even more sick to their stomach.

What stings more about the playoff series loss is Ottawa hasn't returned to the playoffs since. Kunitz has set the Senators back ever since his goal.

1. Jeff Friesen's late third period Game 7 goal helps Devils eliminate Senators in 2003 Eastern Conference Finals

Senator fans often debate the greatest team in franchise history. The 2002-03 Senators could have the edge of being the best team with being the only Senators team to ever win the President's Trophy. Senators legend Chris Phillips named the 2003 team as the best.

After cruising their way through the first two rounds of the 2003 playoffs, the Senators met the Devils in the 2003 Eastern Conference Finals. At the time of the series, the Devils had won two Stanley Cups and played in three Stanley Cup Finals over the past eight seasons, but the Senators appeared ready with their dominate team and having home ice advantage.

The Senators won Game 1 in overtime with Shaun Van Allen scoring the overtime winner, but the Senators dropped the next three games to trail 3-1 in the series. However, the Senators won the next two games, including Phillips scoring the overtime winner on the road in Game 6 in New Jersey to set up a Game 7.

The energy inside Corel Centre for Game 7 was off the charts. The arena was buzzing early when Magnus Arvedson scored 3:33 into the game, but Jamie Langenbrunner scored twice in the second period to give the Devils a 2-1 lead heading into the second intermission.

When Radek Bonk scored 1:53 into the third period to tie the game, the scene was set for an unforgettable finish. Both teams had chances to take the lead, but Patrick Lalime and Martin Brodeur had other ideas. That was until late in the third period.

One name that haunts every Senators fan is Jeff Friesen. With 2:14 remaining in the third period, Grant Marshall got a pass through the skates of Wade Redden and Friesen scored to give the Devils a 3-2 lead. The Devils defense and goaltending prevented a tying goal and the Senators would be eliminated in a brutal way to end the season.

Had the Senators completed the 3-1 comeback, they would've faced the Mighty Ducks of Anaheim in the 2003 Stanley Cup Finals. The Devils won the series in seven games, so Senator fans and the team had the thoughts of "it should've been us" on their mind.

With the 2003 Eastern Conference Final loss happening at home, it makes the playoff series loss worse. It also denied the Senators of making their first Stanley Cup in franchise history.