The cruelty of the penalty: What becomes of football's broken-hearted?

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So near, and yet...and yet. John Terry's dramatic miss in the shoot-out that sealed the Champions League final was a professional calamity and a personal tragedy. But many of football's greats have found themselves in the Chelsea captain's boots. Glenn Moore presents the edited highlights

1. Uli Hoeness

1976 European Championship, final, West Germany v Czechoslovakia (Belgrade)

Before 1970, tied matches in knock-out competitions were decided either by replays or, when scheduling made that impossible, by the drawing of lots. But after Italy reached the final of the 1968 European Championship by the latter method, penalty shoot-outs, already a feature of schools football, were introduced.

The first shoot-out in England was in 1970, in the Watney Cup. George Best took the first kick, and Denis Law, another Manchester United legend, became the first to fail. The man who saved his kick, Hull City goalkeeper Ian McKechnie, subsequently missed the decisive penalty in this shoot-out.

Six years later came the first internationally followed shoot-out, in the European Championship final. West Germany, the World Cup holders, had come from 2-0 down to draw level with unfancied Czechoslovakia, forcing penalties. The first seven were converted. Then, Uli Hoeness, the blond midfielder from the reigning European Cup champions Bayern Munich, stepped up. Hoeness blasted high over the bar. This meant that if Czechoslovakia scored their next penalty they would have an unassailable 5-3 lead (penalties are conducted in two lots of five, taken alternately, and then sudden-death).

Antonin Panenka converted probably the best penalty ever taken, coolly chipping the ball into the middle of the goal while goalkeeper Sepp Maier leapt to his left. Had Maier stood still, the ball would have gone into his arms, but no one had previously taken such a penalty the way Panenka did.

The tournament was Czechoslovakia's only major triumph, either as a unified country or, since 1993, as two independent ones. Germany have subsequently won many tournaments. Hoeness is now the general manager at Bayern Munich.

Terry's Tears rating: *

2. Maxime Bossis

1982 World Cup, semi-final, France v West Germany (Seville)

A rare instance in which the villain is not the man who missed the crucial kick, French left-back Maxime Bossis, but the man who saved it, German goalkeeper Harald "Toni" Schumacher.

The score was 3-3 after extra-time. West Germany's Uli Stielike missed the sixth kick, but then Schumacher intervened. The goalkeeper should not even have been on the pitch. In the second half of normal time, with the score 1-1, Patrick Battiston broke through the German defence on his own. Schumacher raced from his goal and jumped into the Frenchman, making no apparent attempt to play the ball. Battiston needed oxygen before being carried off on a stretcher with concussion, damaged vertebrae and broken teeth. The goalkeeper was not booked, nor was a free-kick awarded. Now, with the world watching on in exasperated fury, he saved from Didier Six, then, in sudden death, from Bossis. Germany went to the final, where they lost to Italy.

Schumacher played, and lost, in the 1986 World Cup final before being dropped after his autobiography made unsubstantiated claims of substance abuse among players. Bossis has worked as a Special Olympics ambassador. Battiston is head of the youth academy at Bordeaux.

Terry's Tears rating: **

3. Stuart Pearce

1990 World Cup, semi-final, England v WEST Germany (Turin)

England, after making an appalling start to the competition, had unexpectedly played their way into the semi-finals for the first (and still the only) time since winning on home soil in 1966. In Turin they met Germany, who were seeking a third successive final. England were outstanding, but conceded an unfortunate deflected goal early in the second half. Gary Lineker equalised with 10 minutes remaining. Extra-time was goalless, but not without drama, Paul Gascoigne crying himself into the hearts of the nation after being booked – which meant he would miss the final if England reached it.

This was England's first penalty shoot-out, so there was as yet no neurosis about the subject. Thus there was an absence of foreboding as the first six penalties were scored – Lineker, Peter Beardsley and David Platt converting for England. Then up stepped Stuart Pearce, a noted penalty-taker for his club, Nottingham Forest. The left-back, nicknamed Psycho for his aggressive tackling, thumped his shot against Bodo Illgner's legs. "My world collapsed," he wrote later. "The walk back to the centre circle was a nightmare as the first onrush of tears pricked at my eyes." England were relying on goalkeeper Peter Shilton to make a save. He failed to stop Olaf Thon, who put them 4-3 ahead. Up stepped Chris Waddle...

Terry's Tears rating: ****

4. Chris Waddle

1990 World Cup, semi-final, England v west Germany (Turin)

The winger had hit the post in extra-time, and was in good form, but, in Stuart Pearce's words, "he put the ball into orbit and we were out of the World Cup". Pearce added: "I don't blame anyone but myself. I was the one who missed first and piled all the pressure on him."

Waddle later said: "There were two ways to react; basically you can do a Lord Lucan and disappear or stick your chest out and prove to everybody you're a good footballer." He went on to do the latter well enough to win the Football Writers' Association Footballer of the Year award in 1993. He also became a folk hero at Marseille before returning to England, where he played until the age of 37.

But unlike Pearce, who continued to take penalties for Forest, Waddle steered clear of the 12-yard lottery until he was obliged to take the 11th kick for Sheffield Wednesday in a marathon shoot-out at the end of an FA Cup tie against Wolves in 1995. His shot was saved. Wolves scored the next to go through and Waddle never took a spot-kick again.

He now works as a pundit for the BBC and writes a newspaper column.

Terry's tears rating: **

5. Roberto Donadoni

1990 World Cup, semi-final, Italy v Argentina (Naples)

Should an Italian player miss a penalty in this summer's Euro 2008 finals, he knows his coach will have only sympathy. Eighteen years ago, in the World Cup, Roberto Donadoni was playing under huge pressure of expectation as the host nation reached the semi-finals. There they faced Argentina, the holders, who had the incomparable Diego Maradona in their ranks.

This was daunting enough, but by an accident of scheduling the match was in Naples, home of Napoli, for whom Maradona played his club football. Naples, moreover, was not as enamoured of the national team as the rest of Italy. Many Neapolitans regarded it as representing a north that looked down on the south.

Argentina had been fortunate to progress, winning their quarter-final on penalties despite Maradona missing a kick. Italy were playing well, if increasingly nervously. They took the lead but could not hold on to it, nor take advantage when a physical Argentina were reduced to 10 men. Come the spot-kicks, Donadoni, who had played well, had his kick, the seventh, saved by Sergio Goycochea. Maradona went next, and scored. Goycochea, only in the team because the first-choice keeper broke a leg earlier in the competition, then denied Aldo Serena to confirm Italy's exit.

Argentina lost an ugly final 1-0 to West Germany. Maradona tested positive for drugs in the 1994 World Cup. Donadoni became Italy manager after their triumph in 2006 and has steered them to Euro 2008.

Terry's tears rating: ***

6. Roberto Baggio

1994 World Cup, final, Italy v Brazil (Pasadena)

The Divine Ponytail, as he became known after converting to Buddhism, had enjoyed a wonderful tournament. He scored five goals in the three knock-out games, including a late brace to rescue Italy from ignominy against Nigeria. One of those excessively talented players who tend to divide opinion, being unable to maintain their elevated standards in every game, this time he had all of Italy pinning their hopes on him.

Baggio, though, was carrying a hamstring injury and struggled like everyone else as the final produced a leaden 120 minutes. Franco Baresi, who returned from injury to give a masterclass in defending, put the first kick over the bar. But Gianluca Pagliuca then saved from Marcio Santos to keep Italy level. Four penalties were successfully despatched before Daniele Massaro had his shot saved. The Brazil captain (now manager) Dunga, scored. Which left Baggio to keep Italy hoping, and put pressure on Brazil's final kicker. He sent the ball over the bar and fell to his knees. Baggio wrote later: "I've never run away from my responsibilities. Only those who have the courage to take a penalty miss them. I failed that time. It affected me for years. It is the worst moment of my career. I still dream about it. If I could erase a moment, it would be that one." Baggio scored in Italy's shoot-out quarter-final defeat to France in the 1998 World Cup. He is now retired.

Five years later, in this stadium, came the most famous shoot-out in women's football. Celebrating winning the World Cup for the USA against China, Brandi Chastain whipped off her top to reveal a black sports bra. The story received almost as much coverage as Baggio's miss.

Terry's tears rating: ***

7. Gareth Southgate

1996 European Championship, semi-final, England v Germany (Wembley)

Another semi-final, again against Germany, another penalty shoot-out. Football in England had blossomed since Italia 90 and Gazza's tears, and Euro 96 captured the imagination, spawning the phenomenon of flags of St George flying everywhere, which has become a feature of international football tournaments.

Terry Venables's team reached the last four on a wave of popular support and produced another epic match, Waddle again hitting the post after Alan Shearer and Stefan Kuntz traded early goals. And so to penalties. We knew Germany had not missed a spot-kick since Hoeness. But this time England matched them, scoring five out of five to push the shoot-out into sudden death. Shearer, Platt, the redeemed Pearce, Gascoigne and Teddy Sheringham scored.

Up stepped Gareth Southgate, who'd had an impressive debut tournament. His shot was weak and Andy Kopke saved easily. Southgate said afterwards that even his mother had asked him why he did not hit it harder.

Andreas Möller, who knew he would miss the final through suspension, then came forward for Germany and nervelessly converted. They went on to win the tournament. England have not reached a semi-final since.

Not long afterwards – and far too soon for many critics – Southgate appeared in a TV advertisement for Pizza Hut with Pearce and Waddle. Pearce later admitted his fee was £40,000. "I couldn't really turn it down," he said later, admitting that he would have turned it down back in 1990.

Terry's tears rating: ****

8. David Batty

1998 World Cup, 2nd round, England v Argentina (St-Etienne)

Two years later, England were on the spot again. Another classic match, another old foe, had been impossible to settle even after extra time. England had produced a performance that was initially brilliant (highlighted by a famous goal from Michael Owen, then 18) and later heroic, following David Beckham's dismissal. The 10 men had matched Argentina for 73 minutes, but the rearguard action meant they were short of natural penalty-takers, who tend to be strikers.

Thus Paul Ince and David Batty, two combative midfielders, were pressed into service. After Shearer, as in 1996, had scored England's first penalty, David Seaman saved from Hernan Crespo. Ince could have put England ahead, but his poor kick was saved by Carlos Roa. Five penalties were converted, leaving Batty to push the series into sudden-death. In the commentary box Kevin Keegan, was asked if he thought Batty would score. Keegan, somewhat put on the spot himself, answered in the affirmative. Seconds later Roa easily saved Batty's kick and England were out again.

Batty is as down-to-earth as any footballer and appeared unaffected by his failure, dismissing it as a bad day at the office. He also admitted it was the first penalty he had ever taken. He played for another decade before retiring with a total of eight goals in 438 league matches.

Terry's tears rating: *

9. Michael Gray

1998 First Division play-off final, Sunderland v Charlton (Wembley)

The play-off to reach the Premier League is the most lucrative game in football, worth anything from £60m to £100m. This year's match, between Bristol City and Hull City, is tomorrow, and spectators at Wembley will be very fortunate if it matches the drama of a decade ago.

Sunderland and Charlton had already played 48 matches to reach this stage. They then shared six goals in normal time, and another two in extra-time, with Clive Mendonca, a Sunderland fan as a boy, scoring a hat-trick for Charlton.

Penalties followed. Often, as in Moscow, players who have performed well during the game miss a penalty. Mendonca, however, firmly scored the opening kick. The next 12 kicks were all converted, so Charlton were 7-6 ahead when Michael Gray, Sunderland's left-back, got the call. Sasa Ilic saved his weak kick.

Sunderland were distraught. On the journey north, manager Peter Reid stopped the coach and ordered the players into a bar. The match, the season and the world were put to rights in an eloquent appraisal. Next season, Sunderland romped to promotion; passing them the other way were Charlton, relegated in their first season. The following year Charlton went back up and stayed up for eight seasons, while Sunderland have yo-yoed. Gray went on to play for England, and is now at Wolverhampton Wanderers.

Terry's tears rating: **

10. David Beckham

2004 European Championship, quarter-final, England v Portugal (Lisbon)

It was not actually Beckham who missed the crucial kick, but he is the one everyone remembers as England, again, failed to negotiate a shoot-out. Beckham had long been England's penalty–taker, scoring the penalty that beat Argentina in the World Cup in Japan in 2002. But he put a penalty high over the bar in Turkey during qualifying for Euro 2004. Then he missed a penalty in the opening game against France.

Nevertheless, as captain, Beckham expected, and was expected, to step up to take the opening penalty after yet another dramatic and controversial tie. Playing the hosts, England had taken the lead, only to lose Wayne Rooney to injury. Twice they were pegged back by Portugal and, as in St Etienne, a "goal" they regarded as the winner was chalked off by the referee.

Beckham, like John Terry on Wednesday, slipped as he took the kick. In Beckham's case he skied it. However, Rui Costa also failed, to level the series. Darius Vassell took the 13th kick. His weak penalty was saved by Ricardo Pereira, who then took off the gloves to smash his own kick past David James.

Terry's tears rating: ****

11. Didier Drogba

2006 Africa Cup of Nations, final, Ivory Coast v Egypt (Cairo)

There has much comment that, had Didier Drogba not been foolishly sent off in Wednesday's Champions League final, he would have taken the fifth penalty instead of John Terry – and Chelsea would have won.

Not necessarily. Two years ago, Drogba took part in a shoot-out which, if anything, was even more significant to him. It was for Ivory Coast in, and against, Egypt, in the final of the Africa Cup of Nations. The 90 minutes were goalless, Drogba missing a good chance with 11 minutes of normal time left. Egypt then missed a controversial penalty in extra time, so the match went to spot kicks.

Essam El Hadari, Egypt's goalkeeper, emerged the hero. Drogba, taking the ninth penalty, had to score to keep Ivory Coast in contention – but El Hadari saved. Drogba was in tears. His dedication to Chelsea has been questioned, but not to the Ivory Coast. With Arsenal's Kolo Toure, he has even been credited with helping to broker the peace deal in the civil war.

Further pain followed, Ivory Coast unexpectedly losing to Egypt in the semi-finals of this year's Nations Cup in Nigeria. The Elephants last won the trophy in 1992.

Terry's tears rating: *****

12. David Trezeguet

2006 World Cup, final, France v Italy (Berlin)

Fortunately for David Trezeguet, his spot-kick failure in the last World Cup final has been overshadowed by Zinédine Zidane's head-butt. The final had been meandering towards penalties for some time when Zidane, inflamed by some ribald comments regarding his sister from Marco Materazzi, butted the defender.

Come the shoot-out, most people were still agog at Zidane's explosion, so his team-mates were probably unsettled. Trezeguet took France's second kick and lashed it against the bar. All five Italians scored, so France's last kick wasn't needed.

There were several ironies in Trezeguet being the culprit. He played for Juventus, of Turin, like many of the victors. Six years earlier, he had come on as a substitute and scored the winning goal against Italy in the final of Euro 2000.

This was the second World Cup in four to be settled on penalties, an unsatisfactory situation that Fifa, the game's world governing body, is seeking to address. Sepp Blatter, the president, said: "When you play a World Cup final, it's all about passion and desire. When you go into extra-time, we're talking about drama. But when we reach the penalty shoot-out, it's a tragedy. Football is a team game, while the penalty shoot-out is all about the individual." A roll call of unhappy footballers, from Uli Hoeness to John Terry, would doubtless agree.

Terry's tears rating: *****

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