A Series of Heartbreaking Losses

How good is sport? Last night we saw two classic (and slightly controversial) finishes as England won the Cricket World Cup after a tied Super Over and Novak Djokovic won a fifth set tiebreaker over Roger Federer at Wimbledon. Of course plenty of attention is going the way of the victors, as they should, but for every classic win, there is a heartbreaking loss.

Safe to say the Black Caps are going to be looking back at a handful of deliveries thinking what could have gone differently. Even someone with 20 Grand Slams like Federer is going to be thinking about the “what it” moments from his epic five set loss. He even had a couple of match points himself to win the tournament.

Just ask any athlete, those losses stay with you and you shudder at the thought of them being brought up over and over and over… so with that in mind let’s take a look at some of the most gut wrenching losses in all of sport.

Andy Roddick – 2009 Wimbledon Final

Let’s start with something we will never see again… at least under the current Wimbledon rules. 10 years ago Roger Federer went five sets with Andy Roddick and it lasted until 16-14 in the fifth set before Federer won. Roddick played the game of his life and fell just short but still had a couple of one liners in the post match ceremony. Remarkably, if you go on YouTube you can actually find the match in full… if you have four and a half hours to kill.

South Africa – 1999 Cricket World Cup Semi Final

While most Australians remember this fondly, South Africans have to think of this as the one that got away. Unconfirmed rumours say Alan Donald’s bat is still lodged in the turf to this day.

Australia – 2006 World Cup Round of 16

Right when Australia and Italy looked set to go to extra time in the 2006 World Cup, Lucas Neill went to ground, Fabio Grosso saw an opportunity and won the decisive penalty for Italy. Francesco Totti converted from the spot, Australia swore in unison and… well some of us are still scarred to this day.

Australia – 2001 World Swimming Championships

Picture this, the 2001 World Swimming Championships and Australia has just won the 4x200m women’s freestyle relay, beating the Americans in nearly world record pace. Naturally they’re quite enthusiastic. In her jubilation, Petria Thomas jumped in the pool… a few seconds before the last team home had finished. Unfortunately that was in violation of the rules and the girls were disqualified. What makes it even worse is seeing the Germans celebrating in the background as the results changed as they were doing their interviews.

Apolo Anton Ohno – 2002 Winter Olympics

Every Aussie loves the Steven Bradbury story, but imagine being Apolo Anton Ohno who was one of the favourites in that 1000m race. Only to get caught up in the wash and see Bradbury crossing the line as shocked as anyone.

Jane Saville – 2000 Olympics 

This one is just plain heartbreaking. Jane Saville was all set to claim gold in front of her friends and family and was disqualified on her way into the stadium. Of course she did claim three Commonwealth golds in her career but… it just wasn’t the same. 


Buffalo Bills – Super Bowl 25

Down 20-19, your kicker lines up a 47 yard field goal to win the Super Bowl… the Buffalo Bills are going to claim their first NFL title. Or not, Scott Norwood’s kick sails wide right and the New York Giants are Super Bowl champions instead. It was one of four straight Super Bowl losses for the Bills, a franchise that could really use a break.

Buffalo Bills – 1999 NFL Wild Card Round

As if that wasn’t enough, the Bills also had the 1999 Wild Card game won, all they needed to do was stop the Tennessee Titans on the kickoff.

Atlanta Falcons – Super Bowl 51

The Patriots bounced back from their crushing loss in Super Bowl 42 with three Super Bowl wins since then, while the Atlanta Falcons are still trying to work out how they went from 28-3 up with 18 minutes remaining to losing 34-28 in overtime. It was over by all accounts, except on the Patriots sideline. Needless to say the Falcons are still wondering what hit them.

Central Coast Mariners – 2011 A-League Grand Final

Poor Graham Arnold (at the time), he had priors with a 2-0 lead in a big game and with four minutes to go, the Roar made the first Orange Sunday something to remember.

Socceroos – 1997 World Cup Playoff

Nope, not getting into this one… as much as Italy hurts to get into, this one is even worse… find your own highlights.

John Terry & Chelsea – 2008 Champions League Final

All John Terry had to do was score his penalty in the shootout and Chelsea would top Manchester United and win the Champions League. Unfortunately for him, it was a rainy night in Moscow.

Leicester – 2013 Championship Playoff Semi Final

With a spot at Wembley on the line, Leicester were about to put Watford to bed as they lined up for a penalty in stoppage time. Manuel Almunia had the moment of his career not only saving the penalty but the follow up as well. In the blink of an eye, Watford flew down the other end and Troy Deeney ended the game. Of course Leciester would go on to win the Premier League three years later.

Kurtley Beale and the Wallabies – 2013 British and Irish Lions Game 1

Admittedly, this series brought about the end of the Robbie Deans era so it wasn’t all bad but as it turns out, that miss did cost them a series win over the British and Irish Lions. We’ll just have to try again in 2025.