Football’s 5 longest penalty shootouts as Villarreal beat Man Utd in 11-10 epic

Manchester United suffered penalty shootout agony in the Europa League final on Wednesday night – but it’s nothing compared to what some sides have been through.

The Red Devils lost out 11-10 to Villarreal, with goalkeeper David De Gea failing to save a single spot kick before missing his own to hand the La Liga side victory.

Remarkably, United’s shootout heartbreak doesn’t even rank among the top five longest spot-kick dramas, which includes entries from the Namibian Cup Final and arch-rivals Liverpool.

Daily Star Sport have taken a long, stuttered run-up and revealed the five most epic penalty shootouts of all time.

KK Palace 17-16 Civics

It took 120 minutes and 48 penalties to decide the outcome of the 2005 Namibian Cup final between KK Palace and Civics.

The game finished 2-2 at the end of extra time, but no-one could have predicted the drama that was to unfold from the spot.

15 penalties were missed in total during a world record shootout that probably lasted longer the game itself.

Olympiacos 15-14 AEK Athens

Villarreal number one Geronimo Rulli isn’t the only goalkeeper to score the winning penalty in an epic shootout.

Olympiacos stopper Antonis Nikopolidis did the same thing in the 2009 Greek Cup against rivals AEK Athens.

His goal handed Olympiacos a dramatic 15-14 shootout win after the sides played out a 4-4 draw in extra time.

Brockenhurst 15-14 Andover

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  • Brockenhurst and Andover share the unusual distinction of being involved in the longest penalty shootout without a kick being missed.

    All 29 spot-kicks had been successfully converted until Andover’s Claudio Herbert’s failed to find his intended target, giving Brockenhurst victory.

    Obernai 15-15 Wittelsheim

    Bad light stopping play is a familiar refrain at Lord’s or The Oval, but it’s an unusual excuse on the football pitch.

    Nevertheless, that’s what happened during a 1997 French Cup tie between Obernai and Wittelsheim which had to be abandoned due to poor light.

    The local FA granted Obernai a bye to the next round on the basis that they were the lower-ranked team and the fixture list was congested.

    Liverpool 14-13 Middlesbrough

    Liverpool won a record-equalling penalty shootout 14-13 to progress to the fourth round of the Capital One Cup in 2014.

    The two sides couldn’t be split after 120 minutes, with Patrick Bamford’s injury time goal levelling the tie.

    It took 30 penalties to separate the teams, before Middlesbrough winger Albert Adomah fluffed his lines to send the Reds through.

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