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Milan 1-1 Juventus: Late Ronaldo Penalty Gives Old Lady Great Result Ahead of Second Leg

Despite AC Milan’s decline in recent years, their matches against Juventus are still widely considered the greatest game in Italian football. Juventus are, of course, the most decorated club in the country with 35 Serie A titles, while Milan share the second place with city rivals Inter on 18. When it comes to Coppa Italia, the Old Lady have 13 of those on their shlef, compared to Milan’s five. On the other hand, the only competition where Milan are above Juventus is the biggest one – the Rossoneri have been crowned European champions seven times, second only to Real Madrid, Juventus ‘only’ twice.

The two teams met on Thursday evening at the historic San Siro stadium in Milan for the first leg of this season’s Coppa semi-final.

Team News

Milan head coach Stefano Pioli was without fullback Andrea Conti who was suspended. He also couldn’t call upon centre-back Leo Duarte, as well as midfielders Rade Krunic and Lucas Biglia, due to injuries.

Gianluigi Donnarumma was in goal. Simon Kjaer and Alessio Romagnoli formed the centre-back partnership, with Davide Calabria on their right and Theo Hernandez on the left. Ismail Bennacer and Franck Kessie paired up in the middle of the park, while Samu Castillejo and Hakan Calhanoglu took up their positions on the wings. Zlatan Ibrahimovic was joined by Ante Rebic upfront.

Maurizio Sarri in the Juventus dugout is probably glad that the experienced Giorgio Chiellini is back in training following an ACL injury, even though the experienced defender still needs to build up but he probably won’t be able to call upon Merih Demiral for the rest of the season due to the Turk suffering the same problem. Danilo, another defender, was also unavailable through injury, as were wingers Douglas Costa and Federico Bernardeschi and midfielder Sami Khedira.

Gianluigi Buffon took the spot between the posts ahead of Wojciech Szczesny. In front of the 41-year-old club legend, Leonardo Bonucci and Matthijs de Ligt held command over the back line, which also consisted of fullbacks Alex Sandro (left) and Mattia De Sciglio (right). Miralem Pjanic anchored the midfield, with Blaise Matuidi and Aaron Ramsey in box-to-box roles. Cristiano Ronaldo, Paulo Dybala and Juan Cuadrado formed a very flexible attacking trio.

The First Half

Milan tried to hit early and in the opening two minutes, first Ibrahimovic headed a Rebic cross wide of the target, and then Kessie blasted one from outside the box with the same outcome. Rebic was next to have a go from range, but his bomb went straight into Buffon.

Juventus, on the other hand, went for a patient approach. They tried to keep the ball in their possession for as long as possible, but the Rossoneri weren’t letting them get away with that. The home team stole the ball in the opposition half a few times but they couldn’t make it count. At the other end, Dybala was involved in the game for the first time in the eighth minute and went down in the box after contact with Bennacer, but referee Paolo Valeri refused to give a penalty.

Three minutes later, Hernandez broke forward down the left for Milan end employed Ibrahimovic in the box. The Swede tried a cunning flick to beat Bonucci and Buffon, but the centre-back read his mind and made a vital block.

So whether Juventus liked it or not, it was a very lively opening to the contest and they had no choice really but to accept the tempo imposed on them and try to match the hosts for energy. It should also be noted that both sets of attackers seemed very inspired to outplay each other. It was, of course, one of the perks of this event to watch Ibrahimovic and Ronaldo on the same pitch, but Rebic and Dybala, to say the least, completely matched the two superstars in giving opposition defenders a lot to think about.

Those defenders, however, were up to the task and there were no real chances at either end. The closest anyone came to scoring in the first quarter was Calabria for Milan in the 22nd minute as his effort from the edge of the box prompted a fine save from Buffon.

Battles in the middle of the park were just as interesting. Ramsey looked particularly lively, but Bennacer was extremely responsible in defending and chased the Wales international wherever he went. On the other hand, Calhanoglu and Castillejo were probably expected to be more involved than they were.

Milan had a sudden chance in the 28th minute as De Ligt made a mess of a pass towards Sandro, enabling Calhanoglu to pick the ball up and involve Castillejo who found Rebic unmarked on the edge of the box. Buffon then saved the shot from the Croatian and at the same time the face of his young defender.

Milan were now gaining confidence and the line of the battle was well in Juventus’ half for long spells. The visitors, when they ventured forward, were mostly only allowed to go wide and whip in crosses which Kjaer and Romagnoli weren’t finding too difficult to deal with.

But the first instance of slackness in Milan’s defending in the 36th minute allowed Cuadrado to shoot from the edge of the box and the Colombian sent it hard and low towards the corner, forcing a great save from Donnarumma.

Nonetheless, the moment obviously boosted the confidence of Sarri’s men and they quickly seized the opportunity to stamp their own imprint on the game. They kept the ball in Milan’s half for minutes at a time. It took the Rossoneri a while to get their act back together, but in the 41st minute, Ibrahimovic won a free-kick 20 yards from Buffon’s goal in a position favorable for a right-footed shooter. Calhanoglu stepped up and hit the wall.

Apart from a fierce protest from Milan players and staff towards the end of the half for what they felt was a foul not being given close to Juventus’ box which resulted in yellow cards for both Hernandez and coach Pioli, there were no excitements for the rest of the half. It’s fair to say that referee Paolo Valeri wasn’t having the best game.

The Second Half

Milan replicated their energetic start to the game after the break, and after Calhanoglu made a mess of a situation inside the box, Rebic broke through and took a shot on target from around 15 yards, but Buffon was again perfectly positioned. Soon afterwards Ibrahimovic failed to redirect a cross from Bennacer towards the goal.

The referee caused another bit of controversy in the 50th minute, by choosing not to give advantage when Milan attacked dangerously after the ball hit Ramsey’s hand. He stopped the play and gave a free-kick which the hosts wasted. Their next attack saw Castillejo have a go from just outside the box, but Buffon seemed unbeatable.

Three minutes later, Juventus threatened for the first time in the second half through Cuadrado, who glided past his marker through the middle and blasted the ball over the bar from range.

Once again, the visitors were forced to raise the tempo of their game, but once they did so, they were able to match the Rossoneri and move the battlefront away from their goal. In the 59th minute, they attacked down the right as De Sciglio broke through and tried to find Dybala inside six yards, but the Argentinian was blocked. Milan hit back quickly though and tested Buffon twice more in quick succession.

The former Italy international saved both efforts, but in the 61st minute, Castillejo whipped in a cross from the right and De Sciglio’s defending on Rebic left a lot to be desired. The former Eintracht Frankfurt winger nicely controlled his volley from the edge of six yards and there was nothing Buffon could do to save his team this time.


Sarri reacted to his team going down immediately by taking out Ramsey and sending in Rodrigo Bentacur in his place.

Juventus now went forward with more determination than before, but by committing bodies forward they left a lot of space for Milan to exploit in behind. In the 68th minute, Ibrahimovic dispossessed De Ligt and a dangerous counterattack could have developed, but at the age of 38 the striker lacks proper pace to run at defenders from a long way from the goal and while he waited for his teammates to join him, Juventus set their defence in order and cleared the danger.

The game was still going pretty much in Milan’s favour, but in the 71st minute, Hernandez was reckless in his challenge on Dybala and the referee waved the yellow card in his face for the second time. Naturally, the red followed.

Both coaches reacted to the unexpected development. Sarri threw his last dice with the introduction of Adrien Rabiot in the place of Matuidi (Gonzalo Higuain had replaced De Sciglio a bit earlier), while Pioli had to add a player to his defensive line and Diego Laxalt entered the fray for Rebic.

Understandably, Milan now had to be content with sitting deep and defending as best they could. It gave Juventus, who were now playing in a 4-4-2 formation with Higuain and Ronaldo leading the line, while Cuadrado dropped to the right defensive flank. In possession, their midfield was a diamond with Pjanic at the base, Rabiot and Bentacur in box-to-box roles, and Dybala behind the two strikers. Off the ball, it fell into a flat line to form a double barrier with the back four.

The changes, combined with Milan playing a man down, worked rather well. They now arrived to the edge of the box with more frequency. Dybala had a lot of freedom in his movements and he made use of it well, constantly trying to either employ a teammate or work up some space to shoot.

With less than five minutes to go, Pioli took out Calhanoglu and introduced Lucas Paqueta for Milan.

And just as it seemed Milan would hold out to take a minimal lead into the second leg in Turin, minute 89 was passing when an attempted volley by Ronaldo hit the hand of Calabria on the edge of six yards. The referee initially refused to give a penalty, but he received a message to check the situation again on the pitch-side screen. Having seen it again, he blew the whistle and pointed to the spot. Ronaldo made no mistake.


With six minutes of added time to go, Juventus now charged forward in search of a winner. Even Ibrahimovic was forced back to defend at this point for Milan, and the scoreline did not change again.

The Afterthought

The immediate impression was – the home team were extremely unlucky to concede so late. They were the better team for most of the contest and probably deserved to win, but it only goes to show what happens when you lower your guard against a team boasting such quality players and a winning mentality like Juventus.

Naturally, nothing is settled after this game, and it was never likely to be. But Milan now have to score in Turin and that will certainly have them motivated to play well again, but it won’t be easy for Pioli’s men at the Allianz Stadium in Turin on March 4th.

Match Report

AC MILAN: Donnarumma 7, Kjaer 8, Romagnoli 7, Calabria 7, Hernandez 7.5, Kessie 7, Bennacer 7.5, Castillejo 7 (80′ Saelemaekers N/A) , Calhanoglu 6.5 (86′ Paqueta), Rebic 7.5 (74′ Laxalt 7), Ibrahimovic 7.

JUVENTUS: Buffon 9, Bonucci 7.5, De Ligt 6.5, Sandro 7.5, De Sciglio 6.5 (70′ Higuain 6), Pjanic 5.5, Matuidi 5.5 (73′ Rabiot 6), Ramsey 6.5 (63′ Bentacur 6), Ronaldo 6.5, Cuadrado 6, Dybala 7.5.

GOALS: Rebic 61′, Ronaldo (P) 90′.

YELLOW CARDS: Ibrahimovic 29′, Ramsey 30′, Hernandez 42′, 71′, Kessie 58′, Castillejo 69, Calabria 90′.

RED CARD: Hernandez 71′.

REFEREE: Paolo Valeri.

DATE & VENUE: February 13, 2020, San Siro, Milan.

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