That hurt. Like, really, REALLY hurt.

Juventus went into the second leg of their Champions League tie with Porto down 2-1 on aggregate and needing to either win 1-0 or, in the absence of a clean sheet, win by two goals, with a 2-1 reverse of the first leg triggering extra time.

The 1-0 scenario went out the window in less than 20 minutes when Porto were awarding a soft penalty and converted to make the aggregate 3-1. Juve’s response was muted at best, and going into halftime it looked like there would be a lot of questions to answer at the end of the night.

But then Juve pulled another second-half turnaround. Federico Chiesa took over, scoring early in the half before a moment of absolute stupidity saw Porto go down to 10 men. Chiesa took over, putting another one into the net to put the aggregate in a flat-footed tie. Juve besieged the Porto goal for the rest of normal time and twice thought they had it won in stoppages, but Porto scraped away and forced extra time. Both teams had nervy moments in the extra 30 minutes, but Porto, clearly playing for a shootout, put themselves back into the lead out of nowhere when Juve played disgraceful defense on a free kick, breaking their wall and allowing Sergio Oliveira to sneak the ball past Wojciech Szczesny. Even then Juve weren’t dead, as an almost immediate response off a corner gave them life, but with the away goals now reversed, they needed another to advance, and they couldn’t find it. The antiquated rule was their downfall for the second consecutive year in the round of 16, in one of the most painful ways possible.

Andrea Pirlo had several players available that he didn’t have in the first leg three weeks ago. Wojciech Szczesny anchored the coach’s usual 3-5-2/4-4-2 hybrid, with Merih Demiral, Leonardo Bonucci, and Alex Sandro playing in the back three. Juan Cuadrado joined Chiesa on the wings, with Adrien Rabiot, Arthur, and Aaron Ramsey in the midfield. Alvaro Morata joined Cristiano Ronaldo up front.

Porto manager Sergio Conceicao played the exact same XI that won him the first leg. Antonin Marchesin sat at the base of a 4-4-2 with Wilson Manafa, Chancel Mbemba, Pepe, and Zaidu Sanusi guarding him. Jesus Corona, Oliveira, Mateus Uribe, and Otavio made up the midfield strake, with Mehdi Taremi and Moussa Marega in the front two.

Juve nearly turned the tie on its head within three minutes when Cuadrado sent in a beautiful cross that Morata walked through the defense to meet at point-blank range. He was trying to simply beat Marchesin with power, but the Argentine threw his hand up and parried it away at point blank range. Porto didn’t look like they would simply sit back and defend, and three minutes after the save Sanusi muscled his way past Cuadrado and crossed for Taremi, whose first shot was charged down. The Iran international followed up and headed the ball toward the corner, but it clunked off the corner of the frame and over for a goal.

The two teams exchanged blows in midfield, with Juve generally taking a little more of the initiative, before the game changed in the 18th minute. It was Taremi who was again in the middle of things, taking a pass from Marega and moving to shield off Demiral. It was perhaps naive of the young Turkey international to make a challenge, but it’s equally true that there wasn’t really enough contact when he did so to warrant a penalty. But Dutch referee Bjorn Kuipers blew his whistle and pointed to the spot. Oliveira sent Szczesny the wrong way and stroked it home to his left, putting Porto up 3-1 on aggregate and Juve firmly behind the eight ball.

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Juve’s response didn’t exactly inspire confidence. Over the balance of the first half it looked like Porto were the more likely to score. Corona and Otavio both tested Szczesny but didn’t come close to beating him. By the 25th minute, Porto had outshot Juve 8-3.

Juve almost got themselves back into the game in the 27th minute when Cuadrado hit another cross from the right. Manafa misjudged it badly and let it fall to Morata, who controlled the ball and fired for the near post, but Marchesin came off his line quickly and made himself big to get the ball away.

But apart from that, there were only two other noteworthy moments in front of the Porto goal, the first a long-range bouncer by Rabiot that forced Marchesin to dive and stop, and the second a flicked-on corner that Marchesin broke out to force away while Bonucci was trying to turn and hit it home. The half ended with Szczesny again being called into action after Juve completely failed to clear a free kick.

Going into the locker room you would be forgiven for wondering where any inspiration would have come from for the Bianconeri. Like in the first leg, the answer came from Chiesa.

Less than four minutes after the restart, Bonucci put a long ball into the left channel. It found Ronaldo with his back to goal. He tried to cushion it down for himself but it got away from him a little. Smartly, he didn’t chase it and left it rolling into Chiesa’s path. The angle was tight, but Chiesa calmly passed it across the face of Marchesin’s goal and into the top far corner. It was a beautiful finish, and suddenly it was game on.

The goal lit a fire under the team, and they were immediately on the attack. Within two minutes they had another shot on target via a stooping Ramsey header. Taremi had been booked in the buildup to that shot, and two minutes beyond that the striker completely lost his head. Marega had been called for a foul on Demiral on an aerial ball, and after the whistle Taremi whacked the ball from midfield into the stands behind the Juventus goal. Juve players immediately swarmed Kuipers, who was of like mind and pulled out his cards, leaving Porto down to 10.

Chiesa almost made the man advantage pay immediately, heading down a long through ball by Rabiot and rounding the keeper, but Pepe bore down on him and managed to disrupt him enough to bounce his effort off the post. But the Italy international wouldn’t be denied and, just after the hour, ghosted away from Manafa and met Cuadrado’s delivery, slamming the header home off the hand of Marchesin.

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Juve continued to press their short-handed visitors. Rabiot forced another save in the 69th minute, and Pirlo sent on Weston McKennie shortly afterward to add some energy and another potential header target. Also off came Bonucci, which could only have been a minutes count move, in favor of Matthijs de Ligt.

Things settled down a little bit, with Juve keeping the ball deep in the Porto half and trying to move it from side to side to pull the Porto defense that little bit apart, while the visitors managed to right themselves and keep from totally tanking. A quick burst came from the visitors with about five minutes left, with Malang Sarr hitting a powerful long shot that Szczesny had to parry, and then Marega slipped the defense on the left side and pulled his shot into the side netting.

Five minutes of stoppage time went up on the board, and in those five minutes Juve thought they had clinched the tie twice. Seconds into the added time Morata split the central defenders and fired past Marchesin, but was correctly flagged offside, as is his lot in life. Then halfway through the stoppages Cuadrado danced past Porto sub Luis Diaz and unleashed a gorgeous left-footed curler from the upper corner of the box. It looked like the perfect cap to the comeback — but then it smacked into the bar and came bounding back.

The game headed for extra time and Mbemba had to jump in to block a shot from McKennie four minutes into the time. Porto presented a big threat when Corona made a sweet turn off a short corner, but his cross wasn’t met with the requisite power by Marega and Szczesny got both hands behind it for an easy catch. The teams switched ends and Juve continued to try to find the last opening they needed, with Ronaldo running on to a pass from Dejan Kulusevski and opting to try to jink his way to a shot instead of finding Kulusevski’s fellow sub, Federico Bernardeschi, down the left side. The shot was blocked, and the quest continued. Another block cam two minutes later when Kulusevski turned Manafa and fired with his right foot from just outside the six yard box, but Mbemba made an excellent sliding block on a shot that could well have gotten past Marchesin. Then Morata got onto a ball that Kulusevski rolled across but hit it right at the keeper when he maybe could’ve controlled for a better shot.

The clock ticked down towards a potential shootout, but with five minutes left Porto delivered the ultimate gut-punch, and it came, as these things have often gone down this season, it came on a self-inflicted wound.

After McKennie was whistled for a really soft foul at the very edge of range for a direct shot, Oliveira lined up to take the kick. Ten yards from him was a three-man wall made up of Morata, Ronaldo, and Rabiot. Oliveira hit it low, and the wall completely fractured. All of them played it like a bunch of kindergarteners, but Ronaldo in particular wussed out, turning completely away from the shooter before he had even hit it. Szczesny was forced to peek around the back end of the wall before he realized where the shot was going, and had to scramble back to his right. He got a touch to it, but it wasn’t enough, and the ball trickled into the goal, sending Porto into utter euphoria.

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Juve needed two goals in five minutes to turn things around—and they got one of them two minutes later when Porto’s marking broke down on a corner and Rabiot was afforded a free header to ram past Marchesin. With the away goals in Porto’s favor, another was necessary. Juve put a few desperate crosses into the box, and with stoppage time practically expired Kulusevski earned one last free kick in the Porto half. Cuadrado took it and Rabiot went up to flick it on, but Marchesin clawed it away from danger with Demiral waiting behind him.

Kuipers blew his final whistle seconds later, and Juve had again been dropped from the knockout round at the first hurdle.

LE PAGELLE

WOJCIECH SZCZESNY - 5.5. Let me be clear here: I consider the free kick to be 75 percent the fault of the wall and their utter failure to defend like professionals. But that still leaves 25 percent to Szczesny, who could have gotten across better to try to interdict that shot, which was pretty hard but not bobbling or anything like that. That one’s gonna keep him up at night. Very good for the rest of the night.

MERIH DEMIRAL - 5.5. The penalty was soft, but Demiral shouldn’t have let himself get suckered into that challenge. It’s something that a guy like Giorgio Chiellini would’ve played more conservatively and avoided giving the ref a decision altogether. Like Szczesny, beyond that play it was a perfectly fine day.

LEONARDO BONUCCI - 6. Made a big block early and made a couple of really good long passes, including the immediate lead-up to Chiesa’s first goal. Had one moment in the box in the second half where he got selfish when Chiesa might’ve been able to put the team in front. He looked unhappy to have been subbed off, but he was probably on a pitch count so soon after injury.

ALEX SANDRO - 7. Made three key passes and spent tons of time in the Porto half supporting the attack, especially after the red card.

JUAN CUADRADO - 9. I thought his presence would make a big difference. I had no idea how much. The man made 12 key passes, put 33 crosses into the box (15 of which were accurate), six dribbles, and had the assist for Chiesa’s second goal. If his stoppage-time rocket had been inches lower, I would’ve been writing an entirely different piece. Oh, and he made six tackles in defense. He was immense.

ADRIEN RABIOT - 6. Turned in a really good shift in midfield. He made a tackle and two interceptions, and put three of his five shots on target to go along with a pair of key passes. His header at the end gave the team life, but he gets a downgrade for his part in the wall fiasco.

ARTHUR - 5.5. Made three tackles in midfield and completed 96 percent of his passes, but only one of them was a key pass and too many were lateral. He did help settle the midfield a little, but didn’t come up with the incisive passes when he needed them most.

AARON RAMSEY - 5. Made very little contribution going forward. This was the kind of game where his ability to supposedly open up a defense would be really important, but it was pretty much non-existent.

FEDERICO CHIESA - 8. He took over the game in the second half. Both of his goals were excellently taken, particularly the first, and he came really close on a couple of other occasions. This kid is exciting, and he gives everything — when he came off late in the first half of extra time he was clearly spent. He needs to be one of the faces of the team going forward.

ALVARO MORATA - 5. Hit the target with all four of his shots, but a couple of them were shots that definitely could have been hit differently. After such a great night on Saturday against Lazio, he was less clinical this time, although his presence did change the way Porto’s defense reacted to the Juve attack and allowed for much more of an aerial presence in the Porto box. Like Rabiot and Ronaldo, he also gets a major ding for the wall issues.

CRISTIANO RONALDO - 4.5. He did f#$& all in this match. Even his assist was more of a missed control than an actual cushioned pass. He barely made an impact going forward in the rest of the game. Even then, this grade would probably be a point or so higher if it wasn’t for his absolute wuss-out on Oliveira’s free kick. He had fully turned away from the ball before his countryman even made contact with the ball, and just blindly jumped instead of knowing where the ball was going. Of all the failures in that wall his was the worst and the most blatant.

SUBS

WESTON McKENNIE - 5.5. Had a couple of shots blocked but couldn’t make the difference in the midfield. He still definitely looks less than fit.

MATTHIJS DE LIGT - 6. Blocked a shot late and won all of his aerials, and even contributed a key pass as Juve pressed for a winning goal.

FEDERICO BERNARDESCHI - 6.5. Made three key passes in 18 minutes of play and put in some excellent corner kicks, including the assist on Rabiot’s goal to give Juve a little bit of life.

DEJAN KULUSEVSKI - 6. Caused some problems for a tired Porto defense and was denied by a great block just before Oliveira’s free kick.

MANAGER ANALYSIS

Pirlo’s day was a bit of a mixed bag.

Whatever he said at halftime certainly got the team going after a disappointing first 45 minutes, and his general ideas for this game were sound. In league play, Porto has had problems dealing with good wing play and crosses, and it was evident from the first few minutes that Cuadrado had been told to exploit that. Juve frequently got runners free in the box on those crosses, and it’s easy to wonder how things would’ve gone if Morata had gotten that first header to either side of Marchesin.

The biggest coaching question I have for Pirlo is why in God’s name he didn’t have a man lying down behind the wall as Oliveira lined up his free kick. That’s practically a given on a lot of free kicks these days, and Cuadrado had done it on Saturday when Sergej Milinkovic-Savic was lining up a free kick. It would’ve been sensible insurance for a breakdown in the wall — which is exactly what happened. Besides that glaring error, I can’t fault Pirlo for much of anything in the way he handled his subs or his general tactics. Juve’s loss in this tie — especially in the first leg — came down to lack of execution amongst the players. It would be a shame for me if this game spelled the end of his Juventus tenure, because with the right moves in the summer I can see things going in the right direction.

LOOKING AHEAD

Juve return to the field on Saturday for a trip to Cagliari, then in midweek will play their rescheduled fixture against Napoli, the result of which will likely determine whether the Bianconeri have any chance in hell of defending their title. Then they welcome Benevento to the Allianz before the international break.