
The Most Heartbreaking Losses in Sports History
Fifteen defeats that still sting, ranked on one axis: how close the loser got, multiplied by what winning would have been worth. Closeness is measured at the last moment the win was theirs to take, whether a strike, a kick, a putt, or a draw they only had to hold. The prize is whatever the win would actually have been, and it ranges from a green jacket to a World Cup at home. That product sets the order and nothing else does, which means a hiding still belongs here and still sinks, because there was never a moment to lose. Every entry is a game, a series or a single tournament with an article of its own, meaning the defeat itself and never the one play inside it, which is why the Bartman ball here points at the 2003 NLCS. Plenty of these are somebody else's greatest day; the camera stays on the side that lost. Setting a cricket final against a Super Bowl is the weak joint in the whole thing, so vote.
- 1
2019 Cricket World Cup Final
Tied on 241 after fifty overs each at Lord's, then tied again in the Super Over, fifteen apiece. Martin Guptill was run out going back for the winning run off the last ball of the match, and England took it on a boundary count back, 26 to 17. New Zealand lost a second consecutive final without anybody outscoring them. Zero margin, biggest prize.
https://en.wikipedia.org/wiki/2019_Cricket_World_Cup_Final - 2
Uruguay v Brazil (1950 FIFA World Cup)
A draw would have done it. Brazil led the final group and only had to avoid defeat, and when Friaça put them ahead two minutes after the interval, in front of an officially recorded 173,850 at the Maracanã, it looked done. Alcides Ghiggia scored with eleven minutes on the clock, it finished 2-1, and the ground went quiet rather than angry.
https://en.wikipedia.org/wiki/Uruguay_v_Brazil_(1950_FIFA_World_Cup) - 3
1986 World Series
Twice the Red Sox stood one strike from a first championship since 1918. Game 6 went to the tenth, Henderson homered off Aguilera for a 4-3 Boston lead, and then a slow ground ball went under Bill Buckner's glove and through his legs into right field. New York won that game 6-5 and the series in seven. A whole era of waiting, undone by a ball that did not bounce.
https://en.wikipedia.org/wiki/1986_World_Series - 4
Super Bowl XXV
Forty-seven yards, eight seconds on the clock, and Scott Norwood's kick sailed wide right by less than a yard outside the upright. Buffalo lost 20-19 to the Giants, and that started a four-game Super Bowl losing streak for a team that kept getting back and never once finished the job. A first title, in their own kicker's hands, gone into empty air.
https://en.wikipedia.org/wiki/Super_Bowl_XXV - 5
2003 National League Championship Series
Five outs. That was all that stood between the Cubs and a first World Series appearance since 1945, holding a 3-0 lead in the eighth inning of Game 6. A fan reached for a foul ball, Moisés Alou did not catch it, Florida scored eight in the inning and won 8-3, and the Marlins took the series 4-3. The fan got the blame, which was never fair.
https://en.wikipedia.org/wiki/2003_National_League_Championship_Series - 6
2011 World Series
Texas were one strike from the first championship in franchise history, and then one strike from it again. David Freese tripled off the right-field wall to tie Game 6, then won it with a home run in the eleventh, 10-9. St. Louis took Game 7 as well. Getting that close twice inside one evening is its own particular cruelty.
https://en.wikipedia.org/wiki/2011_World_Series - 7
2008 UEFA Champions League final
Moscow, the Luzhniki, and the first all-English European Cup final. Cristiano Ronaldo headed United ahead in the twenty-sixth minute, Frank Lampard levelled before half-time, and 1-1 held through extra time. John Terry walked up to win the cup for Chelsea, slipped as he struck it, and hit the post. Van der Sar saved from Anelka to end it 6-5, and Chelsea went home from a final they had a foot on.
https://en.wikipedia.org/wiki/2008_UEFA_Champions_League_final - 8
1999 Open Championship
Three shots clear standing on the seventy-second tee at Carnoustie, Jean van de Velde took off his shoes and socks and waded into the Barry Burn to weigh up playing it out of the water. He holed a six-footer for a triple-bogey seven, which dropped him into a three-man play-off he did not win. One hole, and a lead that could have survived almost anything else.
https://en.wikipedia.org/wiki/1999_Open_Championship - 9
2003 Rugby World Cup final
Hosts, defending champions, and level with the clock dead. Elton Flatley's penalty from fifteen meters with ten seconds left forced extra time at 14-14 at Stadium Australia. Then, twenty-eight seconds from the end of extra time, Jonny Wilkinson dropped a goal off his right foot from thirty meters and England won 20-17. Australia dragged it level and still walked off with nothing.
https://en.wikipedia.org/wiki/2003_Rugby_World_Cup_final - 10
Super Bowl XLII
New England arrived 16-0 in the regular season and left having lost the last game of the year. Eli Manning wriggled out of a sack, David Tyree pinned the ball against his own helmet for thirty-two yards, and Plaxico Burress scored from thirteen out with thirty-five seconds left. Giants 17-14. The 19-0 record they were playing for died right there on the grass.
https://en.wikipedia.org/wiki/Super_Bowl_XLII - 11
1994 FIFA World Cup final
Nobody scored in a hundred and twenty minutes at the Rose Bowl, so a World Cup went to penalties in front of a Pasadena crowd cooking in July. Roberto Baggio blazed the fifth kick over the bar and Brazil won 3-2. He was the player Italy leaned on all summer and he still had to walk up and take it, and the freeze-frame of him afterwards is what survived.
https://en.wikipedia.org/wiki/1994_FIFA_World_Cup_final - 12
1993 NCAA Division I men's basketball championship game
Down 72-71 with eleven seconds left and the rebound in his hands, Chris Webber signalled for a timeout Michigan did not have. Technical foul, two free throws, North Carolina ball, and it finished 77-71. Those sophomores had been to two Final Fours in as many years and walked away from both with nothing. One hand signal, and that is the entire memory.
https://en.wikipedia.org/wiki/1993_NCAA_Division_I_men%27s_basketball_championship_game - 13
1994 Stanley Cup Final
Vancouver went 3-1 down and dragged the series to a seventh game, into the one building in the league where fifty-four years of waiting was screaming at them. They lost 3-2 at Madison Square Garden. With six minutes left Nathan LaFayette put a loose puck off the post behind Mike Richter, and that is the whole story: an inch of iron, on the road.
https://en.wikipedia.org/wiki/1994_Stanley_Cup_Final - 14
1996 Masters Tournament
Six shots clear with one round to play at Augusta National, Greg Norman went out on the Sunday and shot 78. Nick Faldo shot 67 and won by five. Norman gave a six-shot cushion away in a single afternoon, hole by hole, in front of a gallery that stopped cheering and started wincing. A whole round is a long way from the line, and he still had every one of those shots to lose.
https://en.wikipedia.org/wiki/1996_Masters_Tournament - 15
Brazil v Germany (2014 FIFA World Cup)
Five goals in twenty-nine minutes, four of them inside six, and Germany finished it 7-1 in a home semi-final at the 2014 World Cup. It ended a sixty-two-match unbeaten run in competitive games on Brazilian soil going back to the 1975 Copa América. Everything was at stake and none of it was in their hands past the half-hour. Nothing slipped here; it was taken.
https://en.wikipedia.org/wiki/Brazil_v_Germany_(2014_FIFA_World_Cup)





