Five Longest Ever Penalty Shootouts

Some say that a penalty shootout is a horrible way to decide a game but it may depend on the result, or indeed how long it took to get there.


A penalty shootout is the most nerve-wracking, nail-biting climax to any game of football. Usually, it doesn’t take long for one team to buckle, but on occasion, they can become a real endurance test in themselves.

Here are the five longest shootouts of all time.

5 – Holland Under-21s 13-12 England Under-21s – 2007

It’s not just at senior level where England have endured much heartbreak over the years – in the 2007 European Championships, the Under-21s were dumped out after a 12-yard marathon.

Leroy Lita had given England the lead just before half time but Maceo Rigters’ late goal saw Holland take the game to extra time.

Penalties were required and all 11 players on each side took spot-kicks with the scoreline tied at 8-8.

The game was decided when Anton Ferdinand smashed the crossbar with his effort and England suffered another semi-final exit.

4 – Liverpool 14-13 Middlesbrough – 2014

Months after Liverpool came close to winning their first title for 24 years, Brendan Rodgers’ side, minus Luis Suarez, seemed to lose some of their potency.

They faced Middlesbrough in the third round of the EFL Cup with the game ending 2-2 after extra time.

Thirty penalties had been taken before Albert Adomah stepped up to miss the crucial kick, sending his effort wide of the target.

3 – Olympiakos 15-14 AEK Athens – 2009

Even before the seemingly interminable penalty drama, the 2009 Greek Cup final was exciting enough.

After Ignacio Scocco scored a 90th-minute goal which AEK thought would win them the game, Matt Derbyshire (who ironically was involved in the England Under-21 squad for the game above), scored in the sixth minute of added time to send the game into extra time with the score-line at 3-3.

Each side scored once more to send the match to penalties and another marathon ensued.

Thirty-four spot kicks were needed and the unfortunate match loser was Argentine midfielder Agustin Pelletieri.

The match helped solidify Olympiakos’ dominance of domestic Greek football.

2 – KK Palace 17-16 Civics – 2005

Namibia is hardly a hotbed of football but one thing it does have is history when it comes to penalty kicks.

Fans certainly got their money’s worth in the final of the 2005 Namibian Cup where an enormous 48 spot-kicks were required.

Fifteen in total were missed with KK Palace eventually coming out on top.

1 – Old Wulfrunians 19-18 Lane Head – 2021

This Midlands non-league JW Hunt Cup clash is officially the longest penalty shootout of all-time with a staggering 44 kicks needed to reach a result – this one goes in at number one due to the scoreline.

The match finished 3-3 after extra time and penalties were needed but absolutely no-one would have predicted what was to come.

There is always a charming sense of chaos about non-league football in Britain and this shootout saw just about everything.

In the end, it was 27-year-old left-back Jack Marsh, a teacher by trade and son of the club’s secretary Simon, who scored the winner.

Old Wulfs celebrated the win in true non-league style – fish and chips and beers.

Rob has around 20 years journalism experience and has written and commentated on the likes of football, cricket and rugby. He also has an impressive background in racquet sports and regularly provides content on the likes of tennis and badminton.
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