The Friday Five: Footballing Heartbreakers

In the wake of Ireland’s heartbreaking aggregate defeat to France, where Thierry Henry’s handballed assist for William Gallas to score an equaliser in extra time denied a team who had performed magnificently to haul themselves level, we pay tribute to five of the greatest footballing heartbreakers in recent memory.

We start off, perhaps predictably, with the greatest last-gasp turnaround of events in recent footballing history.

1) Bayern Munich – Champions League Final 1999 v Manchester United

Only the most hardened of hearts, or the most ardent of Manchester United fans could not have felt some sympathy for Bayern Munich in 1999 as a three minute spell right at the death wrenched arguably the biggest match in Europe away from their grasp and handed it to a brilliant Manchester United side.

This was undoubtedly the year of Sir Alex Ferguson and Manchester United. He had built a brilliant team, with Peter Schmeichel, Jaap Stam, Roy Keane, Ryan Giggs, David Beckham, Dwight Yorke and Andy Cole all arguably at the peak of their powers. They had managed to clinch victory in the league over a brilliant Arsenal team only on the final day courtesy of a home victory over Tottenham Hotspur, and then brushed aside Newcastle United with ease to claim the FA Cup. Now with the Champions League final, they stood on the brink of a historic treble and for Ferguson it was the chance to win Europe’s biggest prize for the first time.

Yet in their way was Bayern Munich, and by no means a poor Munich team. Oliver Kahn, Samuel Kuffour, Patrik Andersson, Stefan Effenberg, Giovanne Elber, Paulo Sergio and Mehmet Scholl were all immensely talented individuals, who would go on to enjoy future success in Europe’s premier club competion, and were masterminded as a team by another legend of management, Ottmar Hitzfeld.

It was they who took the lead, as a Mario Basler free kick after five minutes gave the underdogs the lead. The response from United was muted, and it was Bayern Munich who were the dominant side-as they twice hit the crossbar, and were denied by Peter Schmeichel, on his final appearance for the club.

manchester_united_v_bayern_munchen Gradually as the second half grew on, they appeared to be heading towards inevitable football. Ferguson, desparate to turn the tide threw on Teddy Sheringham and Ole Gunnar Solskjaer, yet still to no avail. Then in stoppage time, Bayern Munich’s rearguard failed to clear a Beckham corner and the ball was eventually hooked in by Sheringham for United’s equaliser.

After 85 minutes of the lead, Bayern appeared shell-shocked, whereas United were roused, and two minutes later, another Beckham corner was glanced on by Sheringham and Solskjaer, a master predator, reacted quickest to volley home to seal the win and cap a spellbinding late comeback for United.

For Bayern it was the cruellest of blows-85 minutes of potential glory, had gone up in smokes in the space of two minutes. At full-time it was all too much for Ghanaian defender Samuel Kuffour who broke down in tears on the turf, it was all joy for United but heartbreak for Bayern.

2) England – Euro 96 Semi-Final v Germany 1996

southgate-euro-1996Another England v Germany encounter, which was in it’s own unique way a heartbreaker. In truth, it was either this or the tears of Gazza in 1990-both were in their own special way symbolic for a generation of English football fans. Yet it was the defeat of England’s Euro 96 team which stood out as the most poignant.

Euro 96 was, in many ways, a wonderful time to be an English football fan. The song Three Lions became the soundtrack of the summer, English football showed it had the stadia, the passion and the infrastructure to put on a wonderful show of football. And the home nation finally had a team which they could be proud of. In many ways it remains a halcyon time for English football-no English team has come closer to glory since. Alan Shearer emerged as an international class striker, David Seaman became a national hero for his penalty saving heroics, England had a team which played good, attractive football-epitomised by their glorious 4-1 defeat of Holland which really kicked the mood into overdrive.

Yet the tournament will always be remembered for that night in Wembley, and the curse of the penalty shoot out. England had started so well against the Germans, with Shearer, on his way to becoming the tournaments top scorer, heading in an early corner. Yet this was itself a Germany team packed with some high class players. Matthias Sammer, European player of the year, was a high class sweeper, Jurgen Klinsmann-a goalscorer English crowds had seen at first hand, and the playmaking talents of Andreas Moller and Thomas Hassler.

It was not long before the German’s levelled, taking advantage of the enforced absence of Gary Neville, the German’s levelled through Kuntz. England then proceeded to dominate much of the match, without being able to force home their advantage. Extra time came, and suddenly England had two golden opportunities-yet failed to take either. Darren Anderton, managing to reach a Steve Mcmanaman cross could only divert it against a post. Then six minutes later, Paul Gascoigne failed by mere inches to get on the end of an Alan Shearer cross with the goal gaping. In the midst of these chances, Kuntz had risen highest the head the ball in from a corner only for it to be disallowed for a push.

So it was onto a penalty shoot-out, and memories of six years early were hanging in the air. This time however, none of the five mandatory men from either team missed, so it went to sudden death. Up stepped Gareth Southgate, the centre half who had a wonderful tournament, but his spot-kick was saved by Andreas Kopke. It was up to Andreas Moller to score the winning penalty, which he did so with utter aplomb-and the much clichéd German efficiency.

For England it was penalty heartbreak once again, for England fans, this will always be remembered as the time when football almost came home.

3) Italy – World Cup Final 1994 v Brazil

baggior-worldcup94Fate can be a cruel mistress at times, take the case of Roberto Baggio for instance. Here is a man whose career was the envy of many millions of men around the world, whose footballing talents dwarf those of more vaunted, more rewarded individuals, a man whose footballing skills have delighted us for his very unique skill, flair and sheer ability. Yet this is a man whose career will always be remembered for one very sad reason-the World Cup final 1994.

The tragedy of this is that Baggio had been so good. The 1994 World Cup is not one of the more fondly remembered World Cups, yet Baggio had performed wonders to galvanise an Italian team who had succumbed to Ireland in their first match into a unit capable of winning the tournament. He was a player who appeared destined for greatness, already a World Player of the Year, and in the semi-final where his two goals took Italy to the final, he had scored an exquisite goal to give the Italians the lead.

Yet Baggio was not alone in this Italian team, it was a team which boasted the likes of Franco Baresi, Paolo Maldini, Demetrio Albertini and Gianfranco Zola, but Baggio was the star. In the final they would face Brazil-a functional side compared with the legendary selecao of 1970 and 1982, but a side more than capable of winning-and possessing in Romario, a striker of their own capable of moments of sheer genius.

The final itself was a poor event-a non event. Both sides-built with defence in mind, and relying on their respective stars-each needing a goal to become joint level scorers for the tournament-for inspiration, cancelled each other out. The veteran Franco Baresi rolled back the years with a magnificent display alongside Paolo Maldini, while for Brazil, the vastly underrated defensive pair of Aldair and Marcio Santos were equally superb.

Neither side could fashion chances, with Romario and Baggio subdued, and so it came to penalties. The outstanding Baresi missed first, as did Marcio Santos, before Taffarel saved from the Italian Massaro and then Dunga, Brazil’s captain, put them in front. Then it was down to Baggio, Italy’s saviour throughout the tournament, to put them in the lead. His miss was spectacular, as Brazil rejoiced around him, Baggio could only hang his head and think of what so easily could have been.

4) Liverpool – League Championship 1989 v Arsenal

Arsenal+v+Liverpool+league+campaign+1989The most dramatic finish to a league championship ever they say, the most pulsating finale to a league title there has ever been, and while for Arsenal it was one of the greatest nights in their clubs history, as with any story, there are winners and there are losers, and for Liverpool this was a heart breaker like no other in English football.

In fairness, these two had been the standout teams in the league. Arsenal, managed by the iron will of George Graham, whose style as a player was firmly swapped for a cold efficiency and dourness as a manager which made his Arsenal team so successful and built on youth team products like Tony Adams and David Rocastle, and bargain buys such as Lee Dixon and Nigel Winterburn.

Liverpool on the other hand were managed by their own incarnation of the messiah, Kenny Dalglish, whose skills as a player had seemingly transferred into management. His was a team which was settled, and still capable of playing some exhilarating football-as any team which boasted the likes of John Barnes, Ray Houghton, Peter Beardsley John Aldridge and Ian Rush naturally would.

Theirs had been a troubled season, with the Hillsborough disaster, yet one which had still brought them success with an emotional FA Cup victory, and they were looking to add the league title to their haul.

Liverpool had in truth set up this finale with a stirring comeback after being 19 points behind Arsenal in February, and they entered this match knowing that anything but a defeat by two goals or more would be sufficient for them to triumph.
The game itself was an even match, with Arsenal’s strong defence of Adams, Bould and O’Leary stifling any threat from Liverpool’s vaunted attacking team, but they appeared to be offering little in the way of attack. Then Alan Smith, the league’s top scorer and a much underrated striker, headed home a Winterburn freekick.

Suddenly the game was alive, one more goal from other team would be enough to win it. Chances came and went for both sides but still there was no sign of another goal-and it was advantage Liverpool as the game headed into extra time. Then Lee Dixon launched a long ball downfield, Smith flicked it onto Thomas, bursting through from midfield, holding off two challenges and then his own nerves, to flick the ball past the advancing Grobbelaar to give Arsenal their second goal.

Cue delirium, Arsenal had done it, they had not only secured the league title, but had broken a fifteen year hoodoo at Anfield. After such a long season, the destination of the league title had been decided two minutes from the end of the season, for Arsenal it was sweet victory, but for Liverpool it was the most heart-breaking of defeats.

5) Manchester United – FA Cup Final 1979 v Arsenal

alan-sunderland-fa-cup-finalWe started with Manchester United so it’s only fitting that we finish with them. This was an FA Cup final which goes down as a classic, only on the virtue of a mad five minute spell, but what a spell. Five minutes of madness, three goals, potentially three different outcomes, and a wonderful end to what in truth had been a poor match.

It had proved to be Arsenal’s afternoon, for eighty five minutes of this match they had been the dominant team, their dominance exemplified by the superlative skills of Irish playmaker Liam Brady whose touch, skill and passing range was a joy to behold in a game devoid of skill and technique.

It was Brady who set Arsenal on their way, as he instigated the move which saw Brian Talbot finish put the Gunners into the lead, and then it was he who accelerated past two defenders to cross for Frank Stapleton to head home neatly to double their advantage.

United were in total disarray, and never appeared likely to get back into the match, as Arsenal’s defence-led by Pat Rice their captain looked like holding firm. Yet five minutes from the end, and seemingly coasting to victory, Arsenal suddenly let things slip. A Coppell freekick was swept back into the middle by Joe Jordan, which allowed Gordon McQueen to score from close range, and suddenly this match which had been for so long in Arsenal’s grasp was suddenly in the balance.

Arsenal’s concentration had snapped and their nerves were frayed, two minutes later Sammy McIlroy received a pass from Coppell, wriggled away from David O’Leary and Steve Walford to fire his shot past the outstretched hand of Pat Jennings. Three second half minutes, two goals and it was game on once again.

Or was it? They say when their team really needs them, the great players come to the fore, and for Liam Brady here was his time. In truth in the record books, it registers him as neither scoring the goal or even assisting it, but his part in the goal was as crucial as any other. Arsenal were by this point stunned, the momentum and the match had deserted them. Yet Brady had other ideas.

Picking up the ball in his own half, he ran at the United defence, veering one way then the other to deceive the men in Red, as he approached the penalty area, he rolled the ball perfectly to Graham Rix on the left wing. Rix barely had to check his stride so accurate was the pass, and his cross was hanging high to the backpost. The United keeper Gary Bailey stretched out a hand but couldn’t get a touch and arriving unchecked was Alan Sunderland to put the ball into an empty net.

Suddenly the game was Arsenal’s once again, they had lost it, and won it all over again. For United it was a real heartbreaking moment, they had seemingly been out of the match, been resuscitated back into it, and then were firmly, and finally put out of it once again. It was a brilliant finish to a poor match, but a sickening blow for United who had fought back so bravely, only to be denied at the last.

Also Read:
Knockout Kings: 10 of the best European comebacks
When did football last made you cry with joy (or despair)?
Daily Mail’s Footballing Heartbreakers list.

Weekend Betting Tip: Back Liverpool against Manchester City and Arsenal against Sunderland
Sharpen your pitchforks in the name of Thierry Henry


  1. BD Condell 20 November, 2009
  2. kevin fanning 23 November, 2009