Who is the NHL’s most disappointing playoff franchise?

May 28, 2025, 11:00 EDT

Who is the NHL’s most disappointing playoff franchise?

The Stanley Cup Playoffs are designed to generate heartbreak and disappointment.

It’s reality in a league that starts with 32 teams and ends in a 16-team battle royal. Half the NHL’s fan bases support teams that don’t even make the playoff cut. Among those that do, all but one’s story finishes on the wrong end of a handshake and exhausting postmortem. Thirty-one losers. One winner. Right now, that remains the Florida Panthers until a new contender strips their bragging rights.

But expectations are a hell of a drug.

Today, we’re counting down which franchises fall short of the expectations set by their regular season performances. Who will wear the NHL’s crown as most disappointing postseason team?

The Method

It’s easy to insert your favorite team into conversations about failure. But if you root for a lottery team, short-term expectations don’t include playoff wins. Fans of the San Jose Sharks haven’t downloaded playoff tickets in their dreams for a while now. And how crushed could Ottawa Senators‘ diehards be given a respectable first-round showing after an eight-year playoff hiatus? Disappointment is all about expectations.

So, how will we set Expected Playoff Wins?

We’ve gone through the NHL’s last five postseasons and identified that year’s 16 playoff teams. The team with the lowest points percentage in the regular season is assigned one expected playoff win as the floor (i.e., an opening round 4-1 series loss). Then, based on each team’s points percentage and the number of playoffs wins available that year, we assign an expected win value to the playoff field.

Example: the 2025 postseason will produce about 87 total playoff wins, give or take, depending on how the remaining series play out. Dark horses Montreal and New Jersey (.555 points percentage) get one expected win. The Presidents’ Trophy winner, Winnipeg (.707), is assigned 11.7 expected playoff wins. All other playoff teams get a figure somewhere in between based on their records relative to the field.

Combine the last five years and here are the expected playoff wins by franchise given their regular season results. The Stanley Cup winner each year is circled.

If these figures seem low, it’s a stark reminder that there are only 80-some playoff wins available annually for the full 16-team playoff field. That’s room for an average of only five or six wins per team across a logjam of legitimate rosters with visions of Stanley Cup parades.

You’ll also notice there are only 24 teams listed, as eight franchises haven’t qualified for the playoffs in the last half-decade: Anaheim; Buffalo; Chicago; Columbus; Detroit; Philadelphia; San Jose; Utah/Arizona.

The 5 Biggest Playoff Disappointments 📉

Now that we have our expectations set, we can compare actual playoff wins to expected playoff wins. Our five most underachieving teams have each fallen at least 10 playoff wins short of expectations.

#5. Winnipeg Jets

Expected Playoff Wins: 22.4
Actual Playoff Wins: 12
Shortfall: -10.4

You can see in the chart above that the Jets’ expectations are a newer development. Impressively, Winnipeg earned six more wins (108) and seven more points (226) than any other NHL team the last two seasons. Whether you took their Cup hopes seriously or not, they’ve been the most successful regular season force since October 2023. Yet, Winnipeg scratched out just seven playoff wins these last two years — and only a dozen since 2021. Connor Hellebuyck’s save percentage drop (.923 to .865 from season to playoffs!) is hard to look beyond when diagnosing the issues of the last two postseasons.

#4. Washington Capitals

Expected Playoff Wins: 19.1
Actual Playoff Wins: 8
Shortfall: -11.1

The Capitals bookended the last five years with elite results. They were tied for fifth in the NHL (.688) in the abbreviated 2021 season and finished second (.677) this past season. But their recent 4-1 series win over Montreal was the first round they’d won since… their 2018 Stanley Cup. Washington’s retool on the fly has been commendable, and you don’t have look further than their longtime rivals in Pittsburgh to see how difficult that process can be with aging talent around. Still, the Caps winning just eight games in four separate playoff appearances has underwhelmed.

#3. Minnesota Wild

Expected Playoff Wins: 20.2
Actual Playoff Wins: 9
Shortfall: -11.2

A bit of a shocker here. Now, the Wild aren’t a perennial powerhouse. But they’ve quietly iced competitive rosters. Over the five-year window, Minnesota is 12th of 32 teams in points percentage. They even mixed in a 113-point roster in 2021-22. That’s no easy feat. It’s resulted in four playoff appearances. The results? Four first-round exits: Vegas (2021); St. Louis (2022); Dallas (2023); and Vegas again (2025). Wash, rinse, repeat. It shows the dangers of being that good-but-not-great archetype — nine playoff wins spanning five years is dreadfully shy of the 16 necessary in a successful Cup year.

#2. Toronto Maple Leafs

Expected Playoff Wins: 34.9
Actual Playoff Wins: 21
Shortfall: -13.9

Say what?! The Leafs are not the most disappointing playoff team of the last five years? Being the second-biggest letdown (by decimals) won’t result in the Core Four and friends raising a banner this October. But it’s nonetheless surprising. Toronto’s 34.9 expected playoff wins are third behind only Colorado (37.2) and Carolina (35.4). These three teams, plus Edmonton, are the only franchises with four or more expected wins every year in our five-year period.

Now, the Leafs have won playoff games — their 21 postseason victories are ninth since 2021. The problem is that an elite regular season team at the peak of its powers winning 7, 3, 5, 3, and 3 games over a half-decade is a recurring failure. And the four seasons before 2021 yield similarly ugly results without a single deep postseason run. Unfortunately for Toronto, the playoffs don’t award participation ribbons.

#1. Boston Bruins

Expected Playoff Wins: 32.4
Actual Playoff Wins: 18
Shortfall: -14.4

Heavy is the head that wears the crown. It’s easy to forget that Boston last won the Cup in 2011 — that’s now 14 years ago. They’ve mostly been a competitive team since — first or second in their division eight times and 11 postseason trips in 14 seasons. But the playoff results haven’t been there in quite a while.

2022-23 is the primary reason for the Bruins being labelled biggest disappointment. Their 132-point campaign shattered the NHL record held by the 1976-77 Canadiens (with two extra games and five loser points not available in the 1970s). This was a juggernaut — Boston’s 14.9 expected playoff wins nearly broke the methodology given 16 wins is the max. But they famously blew a 3-1 series lead to Florida, losing Game 7 in overtime in the first round. With the highest points percentage (.823) by far in our five-year sample, Boston exited -11.9 wins short of expectations in 2023. An excruciating flop.

Here is a summary of the Bruins’ disappointing half-decade:

2025: Missed playoffs
2024: 109-point team loses Round 2
2023: 135-point team loses Round 1
2022: 107-point team loses Round 1
2021: 107-point team loses Round 2

The 5 Biggest Playoff Overachievers 📈

We’ll wind down by balancing negativity with some positivity. The visual below begins with teams that exceeded their expected wins — the respected playoff performing franchises.

Remaining Cup candidates Edmonton (+15.2), Florida (+14.7), and Dallas (+9.1) crack the top five. The trio has made at least the Conference Finals three of the last four seasons. While all were solid regular season teams, their expected playoff wins rank just fifth, seventh, and ninth, respectively. So, they’ve found some combination of a higher level, suitable style — and some good fortune — come playoff time.

Carolina (-0.4), still alive in the Eastern Conference Final, is the only team to win a round each of the last five seasons. Their 35 playoff wins are third overall, matching the high expectations of a perennial contender.

It should be noted that, with the 2025 postseason still in progress, these four franchises can only rise further on the leaderboard. Each playoff win adds one to the Actual Wins column and therefore the Difference column, meaning the order of the top five could shift entirely by late June.

Montreal’s podium position (+12.4) is exclusively from its 13-win, Cinderella playoff run in 2021 after finishing with by far the worst points percentage (.527) in that year’s playoff field. Tampa (+10.0) remains fourth, still riding the wave of back-to-back Finals appearances prior to its three consecutive first round exits.

Closing Thoughts

By plotting both the expectations and results of the 24 playoff franchises below, we gain insight into what the last five years have been like for each fan base.

Is it better to follow a team with modest expectations that meets or exceeds them in the postseason? Or an elite regular season team with high hopes that consistently falls short? We’ll leave the final say to Bruins’ fans — supporters of the most disappointing playoff franchise of the last half decade.

Visit adjustedhockey.com; data from Hockey-Reference.com

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