Ajax outlasted Panathinaikos in a gruelling penalty shootout that lasted 25 minutes as they progressed to the final stage of Europa League qualification.
The Dutch giants beat Panathinaikos 13-12 in the shootout as the two teams combined to take 34 penalties, setting a UEFA competition record.
The previous record stood at 32 attempts, set by England and the Netherlands in the 2007 European Under-21 Championship.
Both teams combined to miss a staggering nine penalties, five of those coming from Panathinaikos and four from Ajax.
Unfortunately for Ajax forward Brian Brobbey, two of those failed efforts were his.
The 22-year-old would take Ajax’s fifth penalty and had the chance to win it after Panathinaikos winger Daniel Mancini missed his team’s first penalty.
However, Brobbey did not convert as the shootout rumbled on.
English star and Ajax captain Jordan Henderson converted his side’s sixth penalty to get things back on track.
Yet Ajax missed two further chances to win the game as former Chelsea winger Bertrand Traoe and Youri Baas both missed after Nemanja Maksimovic and Sverrir Ingi Ingason had done the same.
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Both teams then converted their next seven penalties, including 40-year-old Ajax goalkeeper Remko Pasveer and Panathinaikos’ Bartlomiej Dragowski.
Brobbey would then have yet another chance to win the game with Ajax’s 16th penalty after Filip Mladenovic missed.
Sadly, it would be a case of déjà vu for Brobbey.
He opted for power but evidently put far too much juice behind his effort as it flew well over the crossbar and into row Z.
Brobbey fell to his knees and slammed the turf below in frustration having blown a second chance to win the contest.
Ajax would quickly have another opportunity to win when Tonny Vilhena missed for Panathinaikos.
Based on the order from the first set of penalties, the stage was set for ex-Liverpool star Henderson to be the hero and score the winner.
Instead, Anton Gaaei stepped up to put an end to the marathon shootout.
Speaking to Dutch broadcaster Ziggo Sport after the game, Henderson revealed why he let Gaaei take the penalty.
“After Brian Brobbey missed, Anton Gaaei said to me, ‘If they score now, you can take it, but if they miss, can I take it?'” Henderson said.
“I said, ‘Sure, go take the glory.’ And he is probably better at penalties anyway. He deserves it, he’s a great lad.”
The contest was forced into a penalty shootout after the tie was locked at 1-1 on aggregate.
Ajax had won the first leg 1-0 on Panathinaikos’ turf, before the Greek club returned the favour inside the Johan Cruyff Arena in Amsterdam.
The Dutch club will now face Polish club Jagiellonia Bialystok in the play-off round, with the winner guaranteed a berth in the Europa League.
Ajax finished a disappointing fifth in last year’s Eredivisie to book a berth in the Europa League qualifiers.
They sat as low as ninth after a horror start in which they won just twice in their opening nine games.
Thankfully interim boss John van’t Schip arrested the worrying slide and stabilised Ajax as they lost only three of their remaining 25 league fixtures.
How the marathon penalty shootout went down
Daniel Mancini MISSES (Panathinaikos)
Steven Bergwijn SCORES (Ajax)
Alexander Jeremejeff SCORES (Panathinaikos)
Branco van den Boomen SCORES (Ajax)
Tete SCORES (Panathinaikos)
Mika Godts SCORES (Ajax)
Tin Jedvaj SCORES (Panathinaikos)
Kenneth Taylor SCORES (Ajax)
Filip Mladenovic SCORES (Panathinaikos)
Brian Brobbey MISSES (Ajax)
Tonny Vilhena SCORES (Panathinaikos)
Jordan Henderson SCORES (Ajax)
Nemanja Maksimovic MISSES (Panathinaikos)
Bertrand Traore MISSES (Ajax)
Sverrir Ingi Ingason MISSES (Panathinaikos)
Youri Baas MISSES (Ajax)
Georgios Vagiannidis SCORES (Panathinaikos)
Anton Gaaei SCORES (Ajax)
Zeca SCORES (Panathinaikos)
Josip Sutalo SCORES (Ajax)
Bartlomiej Dragowski SCORES (Panathinaikos)
Remko Pasveer SCORES (Ajax)
Daniel Mancini SCORES (Panathinaikos)
Steven Bergwijn SCORES (Ajax)
Alexander Jeremejeff SCORES (Panathinaikos)
Branco van den Boomen SCORES (Ajax)
Tete SCORES (Panathinaikos)
Mika Godts SCORES (Ajax)
Tin Jedvaj SCORES (Panathinaikos)
Kenneth Taylor SCORES (Ajax)
Filip Mladenovic MISSES (Panathinaikos)
Brian Brobbey MISSES (Ajax)
Tonny Vilhena MISSES (Panathinaikos)
Anton Gaaei SCORES (Ajax)
Olivia Martin is a dedicated sports journalist based in the UK. With a passion for various athletic disciplines, she covers everything from major league championships to local sports events, delivering up-to-the-minute updates and in-depth analysis.