The incomplete Italian job
A defeat is never a good thing but after the week from hell, Antonio Conte will probably feel that a 1-0 deficit in the cauldron of the San Siro will be at least a surmountable task back in north London.
With recent days having brought long-term injuries to Tottenham captain Hugo Lloris, midfield lynchpin Rodrigo Bentancur, summer signing Yves Bissouma and left wing-back Ryan Sessegnon as well as a dismal display at Leicester, expectations had taken a battering for the trip to Milan.
On top of that, the suspension of Pierre-Emile Hojbjerg meant that Conte had to pair up the inexperienced 20-year-old Pape Matar Sarr and 22-year-old Oliver Skipp in the centre of the pitch for only the second competitive game, having only previously done so against League One side Portsmouth in the FA Cup, after Bissouma felt his ankle flare up during the warm-up.
READ MORE: Tottenham player ratings vs AC Milan: Sarr and Skipp impress but Romero, Son and Kulusevski poor
In the end the two youngsters would be the shining positives in front of the raucous 74,320-strong crowd. If only the more experienced players had followed the energetic tempo the duo in the centre set.
The problem was that for the noisy contingent of travelling Tottenham fans, just over 4,200 of them who made the trip to Italy and sat up in the gods at the San Siro after packing out the streets and canal edges of Milan, it was another performance lacking in any real cutting edge.
Spurs were blunt despite the array of attacking talents available to Conte, the one area currently unaffected by the injury problems.
This was no bad team performance, if anything Spurs handled conceding yet another early goal this season well, but they just offered so little to thrill their fans against a Milan side that, before Friday's 1-0 win against Torino, had not won a game since January 4, taking just two points from 15 in Serie A.
It was Tottenham's first defeat to Milan across five matches in European competition, with the north London side having won two and drawn two of the previous four encounters.
This time it was decided by a single goal, Brahim Diaz given the opportunity to follow up his own shot to score. Cristian Romero had been beaten far too easily by Theo Hernandez to a header in the build-up and the Milan man had time to get to the ball first and drive into the box and fire a cross/shot that Spurs goalkeeper Fraser Forster got in the way of and the ball deflected to Diaz.
Forster made a superb reflex save to stop the attacker's first effort but the ball fell kindly for Diaz to hurl himself forward and head it back past him.
Spurs huffed and puffed but failed to really test Forster's counterpart Ciprian Tatarusanu. The visitors had marginally more of the possession with 53% and had more shots on goal, 12 to Milan's nine with three on target to the hosts' four.
However, it was Milan who could have put the tie to bed late on with Charles de Ketelaere and Malick Thiaw both sending headers inches past the right-hand and left-hand posts respectively. All Spurs could claim in the final moments was a penalty shout for a push on Richarlison that was waved away by the officials.
"As for the performance I think it was a battle from the start until the end," Conte told football.london.
"I think we played against a team with a high intensity and a lot of pressure and it was very difficult to play for us and difficult to play for them. It was a pity to concede a goal after five minutes because I felt in this specific situation we could have done much better.
"Then we tried. When you play against Milan you have to pay attention when you attack to prevent the counter-attack because they have players like Leao and Theo Hernandez and also a point of reference like Giroud. If they have space they can kill you.
"We are now talking about the first game for the qualification and there are two games. I hope, I'm sure, that in the second game in our stadium I know that our fans will create an important atmosphere to push us to overcome the Milan obstacle."
He added: "I think my players have played with willingness, they have determined, they have been there. Conceding a goal after five minutes was really hard for us. The match was all downhill for Milan, after that goal they could play with different characteristics, not with the typical ones.
"They have very good players, like Leao, Theo Hernandez and Giroud, when you make a pass, you hand a pass to Giroud, Giroud makes possession and he allows the team to attack. I am not making reference to only Giroud, I am making reference to the performance of the whole opponent."
Spurs will need to improve on March 8 in their own backyard against Milan to progress to the quarter-finals.
The Sarr and Skipp Show
This was always going to go one of two ways for Pape Matar Sarr and Oliver Skipp.
Either they were going to be overwhelmed by the occasion and din of the 74,320 people inside the San Siro or they were going to thrive on the responsibility and step up for Tottenham.
Thankfully for Antonio Conte, they did the latter. What made it even more impressive was that they did it together, without an experienced, guiding head alongside them which only went to show how mature their games are.
football.london understands the pair really enjoy playing alongside one another, having done so for the full 90 minutes against Portsmouth and briefly during the friendly against a Peterborough U21s side during the Premier League break, while also getting time together on the pitches of Hotspur Way in training games.
That understanding and appreciation of each other showed in Milan. The young duo were organised, they knew each other's game well, when one did get forward the other sat behind to cover.
They complemented each other well and showed absolutely no fear, both looking more than comfortable on such a stage. You would hardly know that it was Sarr's Champions League debut and Skipp's first start in the competition.
The only thing missing was a few penetrative passes through to the forwards but that will come.
Sarr, just 20 but with World Cup and Africa Cup of Nations experience, already has that in-built confidence in his play to try those quick probing passes between the lines and he executed a number of them perfectly, albeit around the middle of the pitch.
He also floated a few pinpoint crossfield passes to the wing-backs as he looked to spread the play. The young Senegal international just needs to transfer those passes to more advanced areas.
Skipp was the workhorse, taking on plenty of the defensive work with his pressing and harassing, winning five duels, although Sarr also did his fair share.
For the 22-year-old Skipp, his confidence grew with every one of those moments when he proved he belonged and by the end of the match he was getting the ball forward quickly and made one burst down the right that resulted in a pull back to Richarlison, who saw his shot blocked.
Allied with an impressive cameo against Preston, Skipp looks to be getting back into the groove and more like the young midfielder who starred during that title-winning season at Norwich as one of the best players in the Championship. Such was his dominance in the Canaries' midfield, he was named in the PFA Championship Team of the Season in 2021.
It's easy to write off time spent at lower level clubs but Skipp's experience at Norwich under Daniel Farke's tutelage really helped shape his game while Sarr was hardened by his experiences in battling against a relegation that eventually came at Metz despite his best efforts as a then teenager.
It all led to this Champions League night in Milan and the pair's stats told their story. Despite his age, Sarr had more touches of the ball (77) and played more passes (59) than anyone else on the pitch, while Skipp was not far behind with 65 touches and 55 passes.
Skipp had a pass success rate of 92.7%, higher than other starting player on the pitch bar Milan centre-back Simon Kjaer (94%). Sarr's pass success rate was 83.1% and he played one key pass to Skipp's two, while also having three shots on goal and one dribble.
Sarr also completed five accurate long balls from his six attempts, while Skipp managed to find team-mates with two of his four long balls and also made one successful cross.
Defensively, Sarr made five tackles and one interception while Skipp made two tackles, one interception and two key clearances.
"I enjoyed every minute of it, not the result we wanted but there is a second leg to come and we are right in the game so we will take the positives," Skipp told BT Sport. "Nice to make my debut, from the start anyway, playing in the Champions League is what you dream of as a kid.
"It wasn't the best start. I think after 10 minutes, it was a goal we didn't need to concede. Neither side created too many chances I feel, but there's a second leg and something to come back from."
On the pair repaying Conte's trust in them, he added: "I think we would have delivered with a win but me and Pape did well and it's nice to have the manager's trust. Hopefully we repaid it.
"There were a couple of times when they were dangerous on the counter attack, threats from forward runners. We had loads of set pieces into the box and created chances. It's only the first leg, we're still in it and we know with our fans that we can make it a dangerous tie at home."
Harry Kane believed the two young midfielders should take a lot of pride away from their performances in the San Siro.
"I though they were both outstanding to be honest. It's not easy to come into the team, two young players who have not got as much experience as some of the others and to come in in this sort of atmosphere and game and perform the way they did, they should be proud," said the striker.
"We were fully behind them and I think it's important that the older or more experienced players make them feel as comfortable as possible. The boss said before the game, we completely trust them and go out there and enjoy playing at the San Siro against one of the more famous clubs in the world. They did that.
"They've been working hard. The players who haven't been playing have been working really hard. After the game you see them running on the pitch, just waiting for their opportunities. I'm sure they'll both be disappointed we lost but they can be proud. We've got a lot of games coming up and I'm sure they are going to play a lot more than they have been. They need to get ready for that."
On Sarr, Kane said: "He's got fantastic quality. I think you saw today he was everywhere. He was breaking up play, tracking back, making tackles, shots, crosses. He's a player who has all the ability and he'll only get better from experiences like tonight, playing a really good team, a really good midfield. We're happy with him. The boss trusts him, that's why he's playing and we're going to need those type of performances for the rest of the season."
The striker added on Skipp: "He's been great. Obviously coming through the academy, he's just a really hard worker. Keeps his head down, works hard, quite shy but just gets on with his job. He was really unlucky. When Antonio first came in, he was playing a big part of our team. He was playing games, looking good, looking solid then he got quite a big injury on his hip or pelvis area.
"That set him back three or four months, and he's just been working hard to get his time again and been waiting patiently so really happy that he's done well tonight. He'll keep trying to improve and that starts again on Sunday."
Conte was delighted with the duo and told football.london that they have left him feeling more relaxed about the lengthy absence of Bentancur and Bissouma.
"I'm really happy about the performance from Skippy and Pape Sarr. Honestly to play in this way in the Champions League and to play in the San Siro in this atmosphere, I think that normally it's tough for important players," he said.
"They played a really good game and I'm really happy. This type of performance make me more relaxed for the future because we have to consider that we could finish the season with only three midfielders, Pape Sarr, Skippy and Pierre Hojbjerg.
"To have this type of performance makes me more relaxed because I know that I can count on these two players 100% and I'm really happy for them."
Bissouma is set to miss up to eight weeks of the remaining 15 of the season following surgery on the stress fracture in his left ankle and Conte was not counting on him as a guaranteed returning player for the final month or so.
"About Bissouma he has a stress fracture in his ankle and when this type of situation happens you never know how long a time he needs to recover," he said. "In my mind, in this moment, is to consider three midfielders.
"To have this type of performance from Skippy and Pape Sarr makes me happy because I have seen a lot of improvement in these players and it means we are working very well with them.
"It means they are improving and for sure they will be the future for Tottenham but at the same time they will be the present. I have to consider them important players and with Pierre Hojbjerg we have only three midfielders.
"Fingers crossed no injuries for the rest of the season and then we hope to recover before the end of the season Bissouma but we know about this situation I'm not sure what is the future and whether he'll be able this season."
This was a big night for Sarr and Skipp despite the result and Spurs fans could be set to see them getting plenty of minutes to flourish in the months ahead. Whatever ends up happening this season, this period might be looked back on as the time when both emerged from the shadows of their more senior team-mates to really set their careers in motion.
The attack needs a jumpstart
Before the match began Spurs went through a series of attacking drills on the San Siro pitch. Sarr and Skipp would play a series of quick passes between each other before beginning one of three scenarios.
One of them would be to pass the ball out to the wing-backs Ivan Perisic or Emerson Royal, who would then cross the ball in for Harry Kane, Son Heung-min or Dejan Kulusevski to head or volley past Alfie Whiteman in the goal.
The second scenario was to feed the ball to Kane, who would spin and shoot and the final part of the drill would see Kane lay the ball off to Son to curl an effort home.
Unfortunately none of that actually came to pass in the match itself as once again Conte's favoured Tottenham's front three were poor.
The Italian media were taken aback by how much such a highly-rated attack struggled. Corriere della Sera said Spurs were "blunt and rusty" while TMW wrote about Tottenham that "going forward they created little or nothing and things did not improve as the match progressed".
Spurs came up against Milan's own two youngsters in defence in 21-year-old Malick Thiaw and 22-year-old Pierre Kalulu alongside the more experienced 32-year-old Kjaer.
Kane attempted to make things happen and he took the hits up front in holding the ball up, but ultimately he was starved of service. The goals have been hard to come by for the England captain in the Champions League despite his Premier League tally, with just one goal against Frankfurt for his efforts across seven matches in Europe this season.
For some reason Dejan Kulusevski's contribution has dropped off a cliff since the World Cup break.
The 22-year-old Swede was an assist machine in 2022 while also chipping in with goals. However, he has scored just twice in 20 matches this season and has not registered a single assist in the Premier League since November, when one apiece came in the final two games before the break after returning from a hamstring injury. On Tuesday night, Thiaw had his number all night.
On the other flank, Son's troubles remain clear. The remarkable stat is that the South Korean star, last season's Golden Boot winner with Mohamed Salah, has scored in just four games this entire season so far, including just two Premier League games.
Conte has gone from getting the best out of Son to being partly responsible for the bluntest version ever seen of the 30-year-old.
The attacker's positioning will not have helped with the data showing that his average position in Tuesday night's match was infield and level with Emerson Royal just past the halfway line and almost alongside Ivan Perisic beside him on the left, while Kulusevski was on average the further Spurs player forward with Kane just behind.
Son is at his best when he is either racing down the wing or centrally as a striker partner for Kane, who drops deep and picks out his runs. Right now, this version of Son is not playing to either strength, with Perisic taking the wing spot and Kulusevski running beyond Kane.
Son's confidence levels have dipped and he's careless in possession at times, particularly poor in working with his back to goal when receiving the ball in his own half, although some might wonder why he's there doing that in the first place rather than pushing forward up the pitch.
On one such occasion at the San Siro, Son was tamely dispossessed, leading to a dangerous counter-attack for Milan and Eric Dier, who will miss the second leg after picking up a third yellow card in the competition, had to slide in and intercept the ball and deflect it for a corner.
While on his knees, the Tottenham centre-back turned and slapped his own legs in anger before launching a verbal volley at his team-mate for losing the ball.
It was Son's 60th European appearance for Spurs, with only Harry Kane (75), Hugo Lloris (70), Steve Perryman (64) and Ben Davies (64) having made more, but it was one of his poorest.
The South Korea captain has every right to be considered among the best players in Tottenham's long history but this is not the real Son Heung-min we're seeing this season. There's little flashes of him and bursts of goals, as seen against Leicester, Frankfurt, Crystal Palace and Preston, but it's not leading to any run of good form.
Conte can't afford to have both Son and Kulusevski misfiring at the same time and there's no real reason why he should be persisting in allowing them to do so with more alternative options than he's ever had before in Richarlison, Arnaut Danjuma and the returning Lucas Moura.
Danjuma scored six goals in the Champions League last season as Villarreal reached the semi-finals, Richarlison was a £60m signing in the summer and Lucas has the experience of scoring in the biggest nights of all.
Conte does not have to hope his attackers play their way back into form. Competition drives players and that's why Richarlison and Danjuma were signed, but they're not getting the minutes to show what they can do beyond little cameos at the end of games.
The Spurs head coach does seem to prefer his customary late substitutions, inadvertently giving the impression that he's waiting or hoping for things to change rather than trying to force them to. Tottenham did not look like scoring on Tuesday night, yet Richarlison did not arrive until the 70th minute and Danjuma with 10 minutes to go.
Perhaps it's loyalty to his longer serving players or perhaps it's trusting Son and Kulusevski to do their share of the defending he requires within his compact system, but it's not working and either Conte needs to change his system to get more out of the duo supplying Kane or he needs to replace them for a game or two to fire them up and gives others a chance before they grow dispirited.
"If you ask me about specific players I can answer you that some of them need to be more self-confident especially when they attack," Conte said after the defeat in Milan.
"They need to recover their trust when it comes to dribbling and attack. I think generally speaking they have been very determined. Now it is my task to show my players that I really trust them and rely on them. We need to try to improve, we need to improve and be prepared for the Premier League and the FA Cup and the second game against Milan."
Takeover talk
Another month has brought another link to Tottenham being taken over or invested in.
This time, the Financial Times have reported that Iranian-American billionaire Jahm Najafi, chair of MSP Sports Capital, are "weeks away" from approaching Spurs about a takeover bid.
The report suggests that such a bid would value Spurs' equity at around $3bn (£2.49bn) before adding roughly $750m (£624m) of debt on to the club's books. The bid is said to be structured so that MSP and its partners would put forward 70 per cent of the purchase price, while backers from the Gulf, mainly from Abu Dhabi, will contribute the remaining 30 per cent.
The interest is understood to be genuine and while neither side have commented publicly, those inside Spurs have denied any approach has been made at this point.
The problem though would also appear to lie in that price tag. ENIC owner Joe Lewis has long been linked with selling the north London outfit and football.london understands that Tottenham are valued internally at beyond £4bn ($4.8bn), far higher than the figures attributed to any potential Najafi-led approach.
It's worth noting that in their last set of accounts, Spurs list their land and buildings assets alone as having a net book value of almost £1.2bn as of 2021.
Since then the value of the huge stadium which cost more than £1bn to construct, the training complex, the club's Lilywhite House headquarters and their various other properties along Tottenham High Road and the surrounding areas will have increased in the past two years on top of any additional land and property purchased and developed.
There is also the potential surge in value of the property when it is factored into the planned regeneration of the Tottenham area.
Any takeover figure would need to take that huge building and land value into account before even starting on the price for a Champions League-playing club that announced revenues of £444m for the last financial year due to that big cash-generating stadium.
There have also been some suggestions by those around the club that chairman Daniel Levy would seek to remain involved in some capacity if the club were to be sold in the future.
Frustrations among Tottenham fans have grown with the ENIC era, leading to some chants for Levy to resign at games this year and small but noisy protests outside the training ground. For all of the improvement off the pitch, the stark fact is that the club has won just one trophy - a solitary league cup - in more than 20 years under the investment company's reign with Levy at the helm.
Some Spurs supporters criticise the club as being more interested in their property portfolio than success on the field, though it's perhaps notable that the Financial Times report on the potential approach from MSP states: "The Najafi-led group's interest in the club extends to real estate and development rights that are available through its ownership."
football.london reported last month amid very early discussions over a minority stake interest from Qatar Sports Investments that it was understood the club had spoken to a number of parties interested in investing in Spurs.
In Tottenham's recently released financial results Levy stated: "The landscape of the Premier League has changed significantly in the last decade.
"It is understandable that some fans call for more spending, much of which is unsustainable for many clubs. We are competing in a league in which we have seen increased sovereign wealth ownership and consortia finance; and in a league where the spending power is now vested in the hands of a few who dominate and have the ability to distort the market.
"We welcome the changes to the governance of the game which will compel greater financial sustainability and financial fair play. Major changes have been introduced in Europe around FFP regulations, including the newly-launched UEFA financial sustainability rules, the full impact of which will be felt from season 2025/26.
"They are based on three pillars: solvency, stability and cost control and clubs will have three seasons to adjust to them. Many expect that these new rules will be a game changer for the sport. Even tighter regulations may follow."
The coming weeks will show whether Najafi's interest does translate into an actual approach and if it does whether the valuation comes anywhere near to Tottenham's.
Recovering Conte and renewed Romero focus
The more immediate issues for Tottenham come on the pitch with Antonio Conte's men needing to get back on track in the Premier League despite their injury woes.
Conte also needs to fully recover as he remains an impaired version of his normally passionate self.
"Frankly speaking in the previous match [against Leicester] I was completely out, I have just had surgery and after two days my doctor told me I couldn't go, I couldn't make effort, so in the previous match I was distant from the pitch," he said on Tuesday night.
"Cristian [Stellini] was there replacing me and was able to share my ideas with the team, he really helped me out a lot. I was wearing a medical device in that period (a post-operative stomach support), but I was still able to interact in a fair enough way with the team, I was not 100 per cent for my physical shape but in the next game I will be fit and try to give my contribution."
Spurs need Conte's fire to return and they need Cristian Romero's to cool ever so slightly. The Argentine defender struggled against Milan, beaten twice by Hernandez in big moments, crucially in the build-up to the only goal of the game.
Yet another reckless late lunge from Romero resulted in a seventh yellow card in seven games since his return from winning the World Cup with Argentina, two of those cards bringing the red that saw him suspended for the defeat at Leicester.
Romero's on-field aggression is both his gift and his curse. It makes him a front-foot defender and Spurs miss the former Serie A Defender of the Year when he's not there. However, that aggression also brings too many cards when it's not curbed.
Romero has gone on similar runs of bookings in previous seasons, but last year Conte made a point of publicly calling for the defender to be controlled in the tackle as he bordered on a suspension and the cards suddenly stopped. Then in the summer the spurs head coach said the 24-year-old needed to have a "hot heart and a cold mind".
Assistant boss Cristian Stellini told football.london last week that the coaches needed to continue to work with the centre-back on the timing of his challenges, without losing the aggression that fuels his best moments.
Conte needs Romero to maintain his focus and some Tottenham fans want the head coach to focus purely on talking about their club.
The Spurs boss has always made it clear that he is completely focused on the job at hand despite admitting that his future remains unclear beyond the end of this season. However, Conte rarely passes up the opportunity to talk about a future beyond Tottenham and that's starting to grate on the fans.
Conte's pre-match press conference on Monday was essentially a love letter to Italian football and after the game at the San Siro a journalist from his homeland asked him whether he enjoyed his return to the stadium and if he would come back to work in Italy.
"Playing here in the San Siro as a player and manager is special, is unique. The San Siro is a historical stadium, it's a beautiful one, it is always packed with people, it is full, and I love the fact whether it is Milan or Inter, the stadium is always crowded," he said.
"It is very good for Milan and the stadium. I am pleased for both groups of fans. Today this beautiful setting was playing against us, the Milan supporters were singing all the time and it is evident they were the 12th man tonight, this will be helpful with us when we play the second leg."
On returning to work in Italy, he added: "I prefer to live in the present, I don't want to think about the future but you perfectly know that as an Italian man and the former Italy manager, Italy is in my heart and Italy will always stay there. I will never exclude the possibility that I will be back here one day, who knows."
It was an honest answer and he was not saying that he was about to jump ship any time soon back to Italy, but having been honest about the difficulties of his family situation, with his wife and daughter back in his homeland, it's not a stretch to think he might want to return there to work.
The problem is the fans don't want to hear Conte being so honest about a life away from their club.
A simple "I'm fully concentrating on my job at Tottenham and at this point I'm not thinking about anything beyond that" would have done the trick without committing to anything more.
The problem also lies in the results and performances being underwhelming. The fans can accept a vision if they see the path it's leading to. When they're not enjoying watching their team it's harder to swallow and that goes for Conte as much as it does for Levy.
Conte proved last season that he can get Tottenham firing on all cylinders, looking like a big team and playing good football. He's more than capable of doing it and that he's defied doctor's orders to come back to work early shows how much he wants to help the club succeed in the months ahead.
Spurs have some big matches coming up, starting with a London derby this Sunday against an improving West Ham side that has lost just one of its past seven games before Conte's old team Chelsea come to visit a week later with their £323m of January signings.
The two games feature a rare free week to prepare between them and with 62,000 fans packed into the Tottenham Hotspur Stadium for both of the games, Spurs and Conte need to give them something to enjoy and believe in again.
At a time when there are questions around the owners, the head coach and the players, these two matches in front of the home faithful could have a major bearing in the direction the season and the mood heads.
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