Maybe we should have known right from the start that this was going to take a while.

Panathinaikos’ Argentinian midfielder Daniel Mancini stepped up to take the first penalty of their shootout against Ajax, the Greek side having scored a late equaliser to force the Europa League qualifying tie on Thursday night to go to spot kicks.

But while he did technically ‘take’ the penalty, he might as well have just blown on the ball for all the force he put behind it when he kicked the thing. A pathetic penalty that 40-year-old goalkeeper Remko Pasveer saved easily was the most appropriate way to start a shootout that featured slapstick, rank incompetence and occasional bursts of excellence.

In total, there were 34 penalties. That, we probably don’t need to tell you, is a UEFA competition record. In all, 25 were scored, two missed the target entirely and seven were saved — five by Pasveer and two by Panathinaikos goalkeeper Bartlomiej Dragowski.

Ajax, who went second in the shootout, had five ‘match points’ — penalties would have won the tie — and flubbed the first four before emerging victorious.

Striker Brian Brobbey was brought off the Ajax bench during extra time, perhaps not explicitly to take a penalty (there were 10 minutes remaining when he came on) but certainly with a shootout in mind. He was one of the 12 players who had to take two penalties. He missed them both. What’s more, both of them were potential clinchers.

Missing one penalty in a shootout will bring deep shame and embarrassment, but you’ll get over it. Missing two is the sort of thing that could haunt you for years. Missing two potential winners… well, at least his side won in the end.

After that first (terrible) penalty from Mancini, the next eight were very smartly taken by, among others, Steven Bergwijn, Kenneth Taylor (both Ajax) and former Leicester City winger Tete (for Panathinaikos).

Then it started to get weird. Brobbey stepped up, and there seemed to be an expectation that he would make short work of this: he isn’t a regular penalty taker, but had only missed one in his senior career and had a prolific conversion rate as an academy player. The home crowd chanted his name, he puffed out his cheeks, hit it with reasonable power to the ‘keeper’s right… and Dragowski saved it. The air left the stadium like it had suddenly become a spaceship’s airlock.

Is it possible to ‘morally’ miss a penalty that you actually score? If so, that’s what the Greek side’s next taker, Dutch midfielder Tonny Vilhena, did. He is a Feyenoord youth product and spent eight seasons in their first team… which is another way of saying the Ajax crowd hated him.

He struck a low kick to Pasveer’s right, and the goalkeeper got down well to get more than a hand (an arm, perhaps?) to it…

… but the ball squirted from underneath him, briefly looked like it might stay out  — to the point that the Ajax fans started to celebrate  — but eventually span across the goalmouth and trickled into the opposite corner.

Vilhena, having heard the thoughts of the home crowd, decided to give a bit back by shushing the terraces. Would this come back to haunt him later on in the shootout? Surely not.

Next up for Ajax was Jordan Henderson, perhaps as much to remind everyone that he still plays for them. Henderson and penalties are not especially good friends: it’s easy to forget because England won, but he missed in their shootout victory at the 2018 World Cup against Colombia, and has since only taken one competitive penalty in regular time for club or country… which he also missed for England in a pre-Euro 2020 friendly against Romania. Happily, he didn’t have any problems here, side-footing straight down the middle and into the net.

GO DEEPER

Jordan Henderson – the serial winner who is now just an idea for fans to hate

Then, another miss: Nemanja Maksimovic erred for Panathinaikos, saved brilliantly by Pasveer. But again Ajax couldn’t take their chance, with Bertrand Traore skewing his effort both high and wide, which is quite difficult to do from 12 yards. It was after this penalty that a squabble broke out in the centre circle, both teams getting tetchy at this extended shootout, and referee Chris Kavanagh booked a player from each side.

The next penalty was Panathinaikos’ Sverrir Ingason, who went low but too close to Pasveer, who bagged his third save. At this stage, he and opposite number Dragowski hugged and started laughing: yes, it was getting quite silly now. And it got even sillier when Ajax passed up yet another chance to win it, as Dragowski saved from Ajax defender Youri Baas.

This was the penalty shootout that nobody seemed especially keen to win. On the touchline, the look on the face of Ajax coach Francesco Farioli suggested he was watching himself undergo open heart surgery. His opposite number, Diego Alonso, looked similar.

However, the next 14 penalties were all excellent, with the goalkeepers barely having a chance. They took kicks themselves and scored with minimum fuss, only ramping up the tension. After all, 14 penalties is a full normal shootout and a half. The Panathinaikos substitutes and coaches, arms locked on the touchline, were told off for encroaching onto the pitch. At some point, Farioli retreated from the touchline and sat alone on the bench, his aorta pulsing about two feet in front of him.

But then, another chance to win it for Ajax: Panathinaikos centre-back Filip Mladenovic tried to go for power, but it was too close to Pasveer who saved to his left.

Redemption presented itself. Just as he had earlier in the shootout, Brobbey strode forwards knowing that if he scored, Ajax would be through. He stepped up, puffed out those cheeks again, resolved not to make the same mistake again — this time, he wasn’t going to let Dragowski get anywhere near it.

And he didn’t — the trouble was that the only people who did get anywhere near it were in the back rows of the Johan Cruyff Arena. Brobbey launched an absolute Chris Waddle of a penalty high into the stands…

… and then proceeded to crumble to the turf…

… face down, unable to believe what he had just done…

… providing a classic ‘you can see the exact moment his heart breaks in two’ moment…

But wait. Here comes Vilhena. You’ll remember from earlier that the former Feyenoord man had shushed the Ajax fans after (just about) scoring his first penalty, which you can understand: he was getting abuse, he scored, and his work was done for the night because there’s no way he would have to take another penalty, right?

Ah. Alas for him, he was facing the extraordinary Pasveer again. The 40-year-old isn’t Ajax’s first-choice goalkeeper, but he took his chance to make an impression here: Vilhena tried the same penalty as his first but this time, Pasveer got more of his body behind it and kept it out for his fifth save.

“Five is quite a lot, yes,” he deadpanned after the game, also saying that he was laughing with former Ajax midfielder Wesley Sneijder, on the touchline working for Dutch TV, during the shootout. “I save a penalty now and then, but I don’t think you often experience something as crazy as this.”

Pasveer last saved a regulation-time competitive penalty in 2021, in the Eredivisie while playing for Vitesse against Heerenveen. The last shootout he was involved in was again for Vitesse, against AVV Swift in the KNVB Cup (Dutch Cup) in 2017. He didn’t save any that night.

Ajax goalkeeper Pasveer celebrates during the shootout (Nikos Oikonomou/Anadolu via Getty Images)

“Remko asked why there was never a picture of a goalkeeper who has kept a clean sheet,” Farioli told AFP, referencing the many photos of Ajax greats that adorn the stadium’s walls. “I told him he should maybe play a bit better. But now I think we should quickly hang up a picture of him.”

Once more, Ajax had one kick to win it. This time they did something interesting: whereas the other players who had taken a second penalty had done so in the same order as the first round, Ajax mixed things up by sending winger Anton Gaaei up for their 17th penalty, in place of Henderson. He went low into the bottom corner, Dragowski went the wrong way and finally, finally, finally, it was over.

From the moment Mancini took the first penalty to Gaaei’s winner hitting the back of the net, 24 minutes and two seconds had elapsed. Ajax won 13-12 and progressed to the play-off round. If they beat Polish side Jagiellonia Bialystok they will qualify for the Europa League league phase.

This wasn’t the longest penalty shootout of all time. That title still belongs to SC Dimona and Shimshon Tel Aviv, who took 56 penalties in the Israeli third-tier play-off semi-final earlier this year.

But from Pasveer’s saves to Brobbey’s brace of misses and Farioli’s utter despair, there was more than enough drama to go around here.

Ajax face NAC Breda in their second Eredivisie game of the season this weekend. You suspect a nice, quiet, boring 1-0 win will do them nicely.

(Top photo: Nikos Oikonomou/Anadolu via Getty Images)