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Ranking the 5 worst Maple Leafs seasons of the past 20 years

The 2025-26 season will go down as one of the top-five worst years in recent Leafs history.
Mar 28, 2015; Toronto, Ontario, CAN; Toronto Maple Leafs defenseman Dion Phaneuf (3) and right wing Phil Kessel (81) warm up before playing against the Ottawa Senators at Air Canada Centre. The Maple Leafs beat the Senators 4-3 in overtime. Mandatory Credit: Tom Szczerbowski-Imagn Images
Mar 28, 2015; Toronto, Ontario, CAN; Toronto Maple Leafs defenseman Dion Phaneuf (3) and right wing Phil Kessel (81) warm up before playing against the Ottawa Senators at Air Canada Centre. The Maple Leafs beat the Senators 4-3 in overtime. Mandatory Credit: Tom Szczerbowski-Imagn Images | Tom Szczerbowski-Imagn Images

The 2025-26 Toronto Maple Leafs season has been a disaster but has it been the worst campaign since the lockout?

For the past nine years, the Leafs have made the playoffs, but for the past five, every fan has essentially said "wake me up in April" as it's been groundhog day. Toronto would finish with 100-plus points, easily make the playoffs and then falter in the postseason.

We definitely took those years for granted as we all expected the same sort of deal when training camp opened last September. Fast-forward six months and this year has been a disaster. A slow start didn't scare anyone as we'd seen it before, but things continued to get worse as injuries piled up one after another and the team's defensive structure was lost.

The Leafs have been outshot essentially every night and will finish the season with the most shots allowed, which is not something you'd think of a Craig Berube coached team. When you think of Berube, you think of a hard-nosed gritty player who is tough to play against every night, but unfortunately that's the opposite of what this team has been.

As a result, let's look back at the worst five seasons post-lockout.

No. 5: 2015-16 season

From a points perspective, the 2015-16 campaign was one of the worst in Leafs history but the only reason it stays at five is because they were trying to tank. After drafting Mitch Marner and William Nylander, the Leafs finally accepted a rebuild and ended up finishing last in the NHL, which resulted in them winning the NHL Lottery and drafting Auston Matthews. The season was ugly but it turned this franchise into a juggernaut for the next decade.

No. 4: 2008-09 season

This is when things start to get sad. The team had zero 30 goal scorers and their best point producer was Jason Blake. Not only that but an aging Curtis Joseph played 21 games that year resulting in the Leafs getting the seventh overall draft pick. Fortunately they ended up using that pick on Nazem Kadri but overall this campaign had zero hope and the team never had a chance at making the playoffs.

No. 3: 2014-15 season

Although this year was the "18-wheeler falling off the cliff" season, it only falls at No. 3 because it was actually the best thing that's ever happened to this franchise. After looking like a playoff team, the Leafs went 5-17-3 in their last 25 games to miss the playoffs, which set up a necessary rebuild. If Toronto somehow made the playoffs that year, we most likely never would have had Marner or Matthews on this team and the future of the franchise would have been totally different.

No. 2: 2025-26 season

After winning the Atlantic Division last year and being considered Stanley Cup hopefuls again, the Leafs fired thier GM and will most likely fire their coach at the end of the season. Not only that but the team was barely able to get any assets at the NHL Trade Deadline this year and the future of the franchise looks unknown. The only sliver of hope is that the team is able to keep their top-five draft pick they traded to the Boston Bruins, but if they somehow fall outside of that, this could end up being the worst year of the past 20 years because of the hope that surrounded them at the beginning of the year.

No. 1: 2009-10 season

After trading their 2010 and 2011 first-round picks to Boston for Phil Kessel, the Leafs finished in second-last place in the NHL this year, gifting the Bruins the No. 2 overall pick which turned into Tyler Seguin. Kessel finished with 30 goals but only 55 points, while a cast of characters such as Niklas Hagman, Alexi Ponikarovsky, Lee Stempniak and Mikhail Grabovski struggled. It felt like Brian Burke was the right man for the job when he acquired Dion Phaneuf and Kessel, as there was a mix of toughness and skill, but the team was awful and this was still the worst year of the past 20 seasons.

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