In the first part of a lengthy series chronicling the most heartbreaking loss for all 124 franchises in the four major North American professional sports leagues, the four teams in the AFC East get the inaugural look.
In the month since the Toronto Blue Jays’ devastating loss in Game 7 of the 2025 World Series, I’ve thought quite a bit about what sports fandom is supposed to be and how experiencing gut-wrenching losses with other fans is a huge part of what makes sports so communal.
Although Toronto’s defeat certainly felt otherworldly in all of the worst ways, it isn’t lost on myself or many other fans across North American professional sports that heartbreakers are simply par for the course when you’re invested as a fan of a given team.
The extent of heartbreak and ensuing jubilation certainly varies by a wide extent. As a Cubs fan, I got to be on the right side of it all in 2016 when the North Siders finally broke a 108-year championship drought, which remains the longest in professional sports history.
While other teams haven’t suffered quite to the extent of not having a championship for over a century, even the most successful franchises have been dealt gut-wrenching losses that at the least, leave fans wondering “what if?” through a disappointing offseason.
As a dedicated sports fan throughout all of my nearly 30 years of life, I figured it’d be fun (and painful, for many fans) to look through all 124 franchises across the NFL, MLB, NBA and NHL and pick out each team’s most painful single-game loss over the past three decades.
Though the losses will certainly vary in severity, as it’d be hard to say any Los Angeles Lakers or New England Patriots fan was “heartbroken” by their team in the last 30 years, every franchise has been dealt a brutal loss that has come with implications far beyond the current season of play.
To start off this series, I’ll be taking a look at the four teams in the NFL’s AFC East division, going through each team’s most heartbreaking loss in my lifetime while tossing in a few honorable mentions for each club as well.
Buffalo Bills: 2021 AFC Divisional Game (42-36 loss to Kansas City Chiefs)
Honorable mentions: 1999 AFC Wild Card Game/Music City Miracle, 2023 AFC Divisional Game, 2024 AFC Championship Game
Though the Bills certainly gave no shortage of options to pick from when it comes to devastating losses, it’s hard to surpass the insanity that was the 2021 AFC Divisional Game in Kansas City.
A rematch of the previous year’s AFC Championship Game that saw the Bills struggle to keep up with Kansas City late, Buffalo appeared more formidable in a back-and-forth duel for the ages.
Arguably one of the greatest sporting events in recent memory, the teams mostly traded blows through the first three-and-a-half quarters, with the Chiefs holding a 26-21 lead with time starting to wind down.
The final two minutes of the game would be about as insane as humanly possible, starting with Gabriel Davis’ third touchdown reception of the game and an incredible two-point conversion pass from Josh Allen to Stefon Diggs to put the Bills up 29-26 with just 1:54 remaining.
While Bills fans may have thought they’d be heading to overtime in a worst-case scenario, Tyreek Hill caught a pass from Patrick Mahomes early in the ensuing possession and had an open field ahead of him, going 64 yards for a go-ahead touchdown that put the Chiefs back in front 33-29 with only 62 seconds remaining in regulation.
Needing a touchdown to stay alive, Allen quickly drove the Bills down the field and completed a record-setting touchdown pass to Gabriel Davis, his fourth of the game, with only 13 seconds remaining to give Buffalo the lead, and seemingly, the victory.
Unfortunately for Bills fans, 13 seconds was still just too much damn time for Patrick Mahomes.
Mahomes completed a 19-yard pass to Tyreek Hill and a 26-yard pass to Travis Kelce after starting the drive at their own 25-yard line, setting up a game-tying 49-yard field goal from Harrison Butker, improbably sending the game into overtime.
Though the results of this game triggered an eventual rules change, none of that mattered on this January night. The Bills lost the overtime coin toss and were essentially helpless on the ensuing drive, with Mahomes going 6-for-6 as he brought the Chiefs down the field and into the end zone to secure an AFC Championship Game berth.
While the Bills have had other heartbreakers, namely falling short by one score to the Chiefs in the 2024 AFC title game and missing a game-tying field goal late against Kansas City in the 2023 AFC Divisional Game, this game stands alone purely due to incredible circumstances. Despite Josh Allen throwing for four touchdowns and 329 yards in a heroic playoff performance, the Bills still came up short due to opposing greatness and surely, some luck on the coin toss as well.
Though the Chiefs went on to lose to the Cincinnati Bengals in that year’s AFC Championship Game, a Bills victory would have given Buffalo an opportunity to host the Bengals in that game, which they would have entered with unbelievable momentum.
If this championship window for Buffalo closes without Josh Allen ever lifting the Lombardi Trophy, this will be the loss that sticks out the most.
Miami Dolphins: 1999 AFC Divisional Game (62-7 loss to Jacksonville Jaguars)
Honorable mentions: 2022 AFC Wild Card Game, 2000 AFC Divisional Game
On the other end from gut-wrenching nailbiters when it comes to heartbreaking losses are embarrassing blowouts where your beloved team never even gave the appearance of being competitive.
Unfortunately for fans of the Miami Dolphins, that’s exactly what they were given in the AFC Divisional round in 1999, the final season for franchise quarterback Dan Marino. While Dolphins fans were hoping one of the sport’s all-time great quarterbacks would lead them to an elusive Super Bowl in his final season, his last game in the NFL was one of sheer disaster.
The upstart Jacksonville Jaguars saw both Mark Brunell and Jay Fiedler throw for multiple touchdowns in a game that saw the Jaguars hold a 24-0 lead after the first quarter. The Jags never truly let off the gas, putting 41 points on the board by halftime while the Dolphins struggled to just keep a drive alive.
The disaster was seemingly immediate for Marino, whose first pass on Miami’s opening drive was intercepted en route to a Jacksonville field goal. Though Marino was able to locate the end zone in a buzzer-beating 20-yard touchdown pass just before the end of the first half, it would serve as the lone highlight for the Hall of Famer’s final NFL game.
Marino went on to make a single four-yard completion on the Dolphins’ opening drive of the second half before being replaced by backup quarterback Damon Huard, who took Miami the rest of the way in what ended up as a 62-7 loss.
In his final NFL game, Marino finished with 11 completions on 25 attempts for 95 passing yards to go with one touchdown and two interceptions, while also taking two sacks for a combined loss of 14 yards.
With the Dolphins being deprived of any consistent success in the years since the Marino era, their last gasp with their all-time great quarterback remains the franchise’s most painful loss in the last 30 years.
New England Patriots: Super Bowl XLII (17-14 loss to New York Giants)
Honorable mentions: 2006 AFC Championship Game, Super Bowl XLVI, 2015 AFC Championship Game, Super Bowl LII
It’s hard to compare this “pain” to that of any other franchise, as the Patriots have been the winners of six Super Bowls in the past 30 years, dominating the league over a two-decade period in a dynasty that is truly unparalleled in pro sports.
With that said, perennial success inevitably creates some heartbreakers along the way, none of which stand out more than the Patriots squandering a perfect season with their crushing loss in Super Bowl XLII to the New York Giants.
Holding a perfect 16-0 regular season record before dismantling the Jacksonville Jaguars and San Diego Chargers in the AFC Divisional Game and Championship Game, respectively, the Patriots were met with a rematch of their final game of the regular season, which they narrowly won 38-35.
Differing from the widely watched slugfest that closed out the regular season, Super Bowl XLII was a defensively-minded duel that entered halftime with a 7-3 score in favor of the Patriots.
After a scoreless third quarter, Eli Manning converted on a five-yard touchdown pass to David Tyree early in the final frame to give New York a 10-7 lead with just over 11 minutes to go.
Following a fruitless drive from New England and a three-and-out from New York, the Patriots drove down the field late in the fourth quarter, with Tom Brady connecting with Randy Moss for a go-ahead touchdown with just 2:45 remaining in the game.
With the Patriots now up 14-10 and on the precipice of an undefeated season, Eli Manning and the Giants embarked on a heroic drive, highlighted by a 32-yard reception from David Tyree in which he used his helmet to maintain possession of the ball to convert on a massive third down.
Eventually getting into the red zone, Manning found Plaxico Burress past the goal line for a 13-yard go-ahead touchdown with just 39 seconds remaining.
Though New England only needed a field goal to tie, the Patriots quickly went three-and-out on their final drive as the Giants completed one of the greatest upsets in North American pro sports history.
Though Patriots fans have been spoiled more than fans of perhaps every other fanbase, many still look back on just how close the team was to completing an undefeated season, which would have surely solidified their status as the greatest team of all-time.
New York Jets: 2010 AFC Championship Game (24-19 loss to Pittsburgh Steelers)
Honorable mentions: 2009 AFC Championship Game, 1998 AFC Championship Game, 2004 AFC Divisional Game
As the Jets have spent the past 15 years mired in mediocrity at best and futility at worst, their most painful loss in recent memory is also their most recent playoff game, the 2010 AFC Championship Game.
Appearing to be an upstart contender in the AFC, the Jets had previously fallen just short of the Super Bowl in 2009, losing to the Peyton Manning-led Colts in that year’s AFC title game before making their way back in 2010.
In 2010, the Jets entered the AFC title game with a hint of destiny and inevitability. After exacting their revenge against the Colts in a narrow AFC Wild Card Game victory, the Jets stymied the archrival New England Patriots in the AFC Divisional Game, taking down the 14-2 Patriots in Foxborough to head to their second consecutive AFC Championship Game.
Though the first half was an unmitigated disaster for the Jets that saw them enter the locker room trailing 24-3, New York feverishly fought back in the second half with their title hopes on the line. Former Steelers Super Bowl hero Santonio Holmes converted on a 45-yard touchdown reception from Mark Sanchez in the third quarter to get the Jets back within two scores.
A safety early in the fourth quarter brought the Jets within 12 points, with the Jets scoring a touchdown on the ensuing possession to make it a 24-19 game with 3:09 left in regulation.
Despite having all three of their timeouts and being on the plus-side of the two-minute warning, the Jets were unable to halt Ben Roethlisberger and the Steelers, who nabbed two necessary first downs to secure the victory and ensure the Jets wouldn’t get the ball back.
After being a mere possession away from the Super Bowl, the Jets have failed to return to the playoffs since, only posting one winning season (a 10-6 record in 2015) since their loss in the 2010 AFC title game.
Leave a Reply