AC Milan took a step towards their first Champions League quarter-final appearance for 11 years as Brahim Diaz’s goal gave the Italians a 1-0 win over Tottenham Hotspur in their last-16 first leg at the San Siro.
The Spaniard headed in a rebound in the seventh minute after a superb double save by Tottenham’s second-choice keeper Fraser Forster and the seven-time winners kept the Londoners at bay.
Spurs, weakened by injuries and suspensions, responded positively in the first half to dominate possession but were unable to seriously worry the hosts. Milan should then have increased their advantage after the break with substitutes Charles De Ketelaere and Malick Thiaw both wasting glorious headed chances.
Tottenham sent on Brazil forward Richarlison for the last 20 minutes and, while they were unable to avoid a first-ever defeat by Milan, they will head home still hopeful of turning the tie around and reaching the last eight.
Relive all the action from Milan 1-0 Tottenham, below.
The Champions League is back – and the Premier League is primed to dominate
As managers such as Stefano Pioli and Marco Rose try to work out how to set up against English clubs for the Champions League’s returns, executives across the competition’s clubs are actually thinking in similar terms. Such is boardroom fear of Premier League power that there is now an increasing refrain in meetings: “Something must be done.”
It remains to be seen whether that something will be the Super League that was relaunched last week and is intended to supplant the Champions League itself. It is nevertheless a feeling that frames the knockout stages, especially amid the expectation that at least three English clubs will get through from the last 16 for the fourth time in five years.
Something very significant did actually happen in the Premier League itself, of course, that could well influence this future. Manchester City were charged with multiple breaches of the English competition’s rules, and essentially accused of fraud. That at least changes the atmosphere around another core theme going into these knockout games.
The last-16 fixtures are the first in the Champions League since the World Cup, and it could also be said that also means they represent the first of a new era in football.
Champions League knockout stage preview, by Miguel Delaney
All four Premier League clubs have their own on-pitch challenges right now but their financial might still dwarfs much of the competition at Europe’s top table
Jamie Braidwood14 February 2023 19:13
Milan vs Tottenham
Here are Tottenham - they are facing AC Milan for the first time since 2011 tonight, but they played at the San Siro two seasons ago against Inter.
Jamie Braidwood14 February 2023 19:03
Is Antonio Conte too stubborn to improve his Champions League record?
For a self-proclaimed winner, it is a return to the place he last won. Two seasons in the dugout at San Siro brought Inter Milan’s first Scudetto for 11 years. It is the sort of achievement that burnished Antonio Conte’s image of himself. He has five league titles in his last seven full seasons in club football. Jurgen Klopp, Thomas Tuchel and Carlo Ancelotti, to name but three, cannot claim as much.
If they are placed on a higher managerial plane, deemed among the real elite, it is because of the Champions League. Facing AC Milan takes Conte back, and not merely because he is a former Juventus and Inter manager. His last Champions League final was against Milan: 20 years ago, when he was a Juventus substitute and they lost on penalties at Old Trafford. It was also an all-Serie A final, something which feels implausible now, when Milan are outbid by Bournemouth for players, when Conte’s stuttering Tottenham are arguably favourites in a two-legged tie against the reigning Italian champions.
The gap on Conte’s CV lies in Europe. Not as a player: during his Juve career, they reached four Champions League finals and he played in three, winning one. But as a manager: he has never reached the last four.
The Tottenham boss returns to Italy tonight but a lack of success as a manager in Europe is underpinned by a lack of a Plan B. Can he adapt his thinking to change his Champions League fortunes?
Jamie Braidwood14 February 2023 18:56
Milan vs Tottenham: Confirmed line-ups!
As expected, Tottenham look very short in midfield with Bentancur and Bissouma injured and Hojbjerg suspended. Antonio Conte has one solution left and goes with Oliver Skipp, 20, and Pape Matar Sarr, 22, as his midfield pair.
Tottenham look strong up front with Kane, Kulusevski and Son all starting, while Clement Lenglet is preferred to Ben Davies at left centre-back.
What a night it is too for goalkeeper Fraser Forster, who stands in for the injured Hugo Lloris. The 34-year-old previously played in the Champions League with Celtic.
Antonio Conte says he is still not 100 per cent following gallbladder surgery but added it’s important to be back with the team in difficult situation
“For sure, it was really difficult to stay far from the team,” he said.
“Because you have a sense of responsibility that you want to stay every moment with your players, to breathe the environment in every situation.
“But this problem happened and now I’m feeling much better than before.
“I’m not still 100 per cent but I think I’m recovering well, it’s very important for me to stay with the team, work with them and try to stay together in a difficult moment for us.”
Jamie Braidwood14 February 2023 18:28
Milan vs Tottenham
Antonio Conte effectively confirmed Oliver Skipp and Pape Matar Sarr will start tonight at the San Siro
“We have the solution in our house, with the two young players, Skippy and Pape Sarr.
“You know we are talking about two young players, their first game in the Champions League, they are really young - 20 and 22 years old.
“Especially for this reason we have to be good to help them to overcome the emotion, and then we trust them.”
(Getty Images)
Jamie Braidwood14 February 2023 18:14
Milan vs Tottenham: Conte suggests some Spurs players collapse under pressure
Antonio Conte has suggested some of his Tottenham players are prone to collapsing under pressure ahead of tonight’s last-16 first-leg tie at AC Milan.
Conte, who says he is still not 100 per cent following gallbladder surgery, watched his side beat champions Manchester City and then follow it up by being thrashed 4-1 at Leicester at the weekend, when a spot in the Premier League top four was theirs for the taking.
Spurs have notoriously failed in big moments over the years and Conte has hinted some of his players cannot live with the pressure.
“If you want to win or achieve some targets and have a good position in the Champions League or in England in the Premier League you have to be stable,” he said. “And this stability is lacking this year. I always talk about it with my players. It is very difficult to keep concentration, it is very difficult to stay focused all of the time.
“It is not an easy task being so focused. We are working on that, playing under pressure all of the time is good for some players and bad for others. Sometimes players feel motivated, other times they feel so much under pressure that they can’t perform.
“Maybe for a period they have a good performance and then they collapse all of a sudden if they feel too much pressure. We are working on this, we want to make our players more resilient.”
Antonio Conte has suggested some of his Tottenham players collapse under pressure (Zac Goodwin/PA) (PA Wire)
Jamie Braidwood14 February 2023 17:58
Milan vs Tottenham
Milan boss Stefano Pioli thinks his side, the current champions of Italy, are equal to Spurs.
He said: “We believe we’re equal to Tottenham. Winning the Champions League is a dream but it’s useless to think about it now.
“A week ago, they beat Manchester City, but we don’t come in better or worse than them. It will be a big game that we will have to play well.”
(Getty Images)
Jamie Braidwood14 February 2023 17:52
Milan vs Tottenham: Early team news
Spurs face a midfield crisis with Rodrigo Bentancur ruled out for the rest of the season after the midfielder ruptured his anterior cruciate ligament in the fixture against Leicester.
Yves Bissouma is also injured while Pierre-Emile Hojbjerg is unavailable through suspension. Captain Hugo Lloris and left-back Ryan Sessegnon also miss out through injury.
Milan are boosted by the return of Fikayo Tomori and Ismael Bennacer but remain without Alessandro Florenzi, Sergino Dest, Zlatan Ibrahimovic and Mike Maignan.
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