The Worst Penalty Fails in Soccer History

November 22, 2010
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The Worst Penalty Fails in Soccer History

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It's been four months since Ghanaian striker Asamoah Gyan missed this critical penalty at the death of the 2010 World Cup quarter-final against Uruguay, a kick that could have sent an African team to the semis for the first time ever. Today, Gyan turns 25, and while he's fortunately moved past his summer of regret—he's currently scoring plenty for Sunderland and dancing all the way—his South Africa penalty fail will no doubt be in the first paragraph of his obituary. That's the thing with botched penalties. As with free throws (Nick Anderson) or field goals (Scott Norwood), the players who miss them at crucial moments tend to loom larger in our collective memories than the ones who convert them. So, then, to "celebrate" Gyan's 25th, we've compiled a countdown of The Worst Penalty Fails in Soccer History, from Baggio and Becks to lesser-known players across Brazil and Britain. Get a hold of your nerves and head to the spot...

12. Robert Pires

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MATCH: Manchester City v. Arsenal

DATE: 10/22/2005

COMPLEX SAYS: Pires and Thierry Henry were trying to recreate this moment of penalty magic from Johan Cruyff. Instead, they ended up looking like...what do they look like? "They look like a couple of dorks." (c) QT in Pulp Fiction

11. Peter Devine

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MATCH: Lancaster City v. Whitley Bay (HFS Northern Premier League Division One Cup Final)

DATE: 1992

COMPLEX SAYS: Remember what we said about the infamy of missing an important penalty? Devine's Wikipedia entry is all of three sentences long, and two of them refer to the cock-up above. We guess it's better than not being remembered at all.

10. Djalminha

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MATCH: Flamengo v. Sao Paulo (Indoor football)

DATE: 2009

COMPLEX SAYS: Like the Pires-Henry fiasco, this penalty was so close to being amazing...and yet, so far. It's the risk/reward thing of trying something crazy in a real match. The risk? Ending up on a Complex FAIL list.

9. Cristiano Ronaldo

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MATCH: Barcelona v. Manchester United (Champions League Semi-final First Leg)

DATE: 4/23/2008

COMPLEX SAYS: OK, this wasn't that bad of a penalty, and United ended up winning the tie anyway, but it's always a little enjoyable to see a CR7 fail. Anyway, at the rate he scores off the pitch, we're sure a few penalty misses won't kill him.

8. Alessandro del Piero

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MATCH: Juventus v. Aston Villa (Peace Cup Final)

DATE: 8/2/2009

COMPLEX SAYS: Just a preseason tournament, but still one of the weakest penalties we've ever seen. The cackling commentator certainly enjoyed it.

7. Mehmet Aurelio

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MATCH: Gimnastic v. Real Betis

DATE: 5/15/2010

COMPLEX SAYS: Like a basketball player who bewilderingly stares at his hands after an airball, a soccer player has to check his feet after slipping on a penalty. Don't hate the appendage, homie. Hate yourself.

6. William

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MATCH: Botofogo v. Fluminense (Copa Sulamericana)

DATE: 9/14/2006

COMPLEX SAYS: We thought Del Piero's penalty was the weakest...until we saw this one. Hang your head in shame, William. That's a FAIL.

5. Martin Palermo

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MATCH: Argentina v. Colombia (Copa America)

DATE: 7/4/1999

COMPLEX SAYS: Palermo made the Guinness Book of World Records for missing three penalties in this group-stage match of the 1999 Copa America. Argentina lost, 3-nil. Do the math.

4. Landon Donovan

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MATCH: Los Angeles Galaxy v. Real Salt Lake (MLS Cup 2009)

DATE: 11/22/2009

COMPLEX SAYS: Missing a penalty by kicking it weakly down the center is a sign that the player lacks confidence; skying it over the bar, like Landycakes did here, means that the player might be a little overconfident. His goal against Algeria in South Africa proved without any doubt that he's a clutch player, but Donovan's miss in last year's MLS Cup helped Real Salt Lake raise the trophy.

3. David Beckham

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MATCH: England v. Portugal (UEFA Euro 2004 Quarter-finals)

DATE: 6/24/2004

COMPLEX SAYS: We had to leave the entire build-up to this epic miss by Beckham, which contributed to England's quarter-final capitulation to Portugal. It was Becks' second penalty miss of the tournament, and one of the worst in his career. You can't even call that a "shank"—it was a goddamn machete.

2. John Terry

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MATCH: Chelsea v. Manchester United (UEFA Champions League Final)

DATE: 5/21/2008

COMPLEX SAYS: If the Chelsea captain had converted the penalty above, the Blues would've lifted the jug-eared trophy for the first time in their history. Alas, he slipped, fell, and cried. Poor John Terry. At least you can find solace in the arms of your former teammate's wife.

1. Roberto Baggio

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MATCH: Italy v. Brazil (FIFA 1994 World Cup Final)

DATE: 7/17/1994

COMPLEX SAYS: The Divine Ponytail had a good overall tournament, and two other Italians also missed penalties in this shootout...but all people will remember about the 1994 World Cup is Baggio's fail. It may be the most notorious penalty miss in soccer history.