Tottenham set to face a struggling AC Milan side at the PERFECT time

ALVISE CAGNAZZO: Divock Origi and Fikayo Tomori aren’t firing, goalkeeper Mike Maignan’s injury lay-off has become a major issue, and manager Stefano Pioli can’t find the right solutions… this is the PERFECT time for Tottenham to play AC Milan

  • Tottenham are set to face AC Milan in the Champions League on Tuesday night
  • Milan have been in dismal form, and have dropped out of the Serie A title race 
  • Antonio Conte’s side couldn’t have asked for a better time to play the Rossoneri

There is no better time for Tottenham to face AC Milan. Stefano Pioli’s team are going through a very difficult moment and the painful 1-0 victory against Torino on Friday perfectly captured the psychological limits of a team that seems to be severely lacking in confidence.

The defeats by Sassuolo, Lazio and Inter Milan in the derby were major blows for the team and above all jeopardised Pioli’s position. 

The Milan coach appears lonely on the touchline, abandoned to his fate and running out of ideas in the eyes of the fans, despite moving away from his preferred 4-2-3-1 system to play a 3-4-2-1.

Milan’s problems arose in the summer and exploded like a time bomb in the autumn. Last summer’s transfer market didn’t allow for an upgrade of the team’s technical prowess, while the side’s engine room has become a problem following the departure of Franck Kessie to Barcelona. 

Pioli is now reorganising the team, especially in defence, because he does not trust his backline to manage matches. The four-man defence has not worked in the opening weeks of 2023, prompting a switch to a back three.

Stefano Pioli’s AC Milan have endured a poor start to 2023, and he’s struggled to find solutions

Can Pioli outsmart Conte?

Tottenham may fear Milan’s history in decisive moments, as the Rossoneri have a habit of triumphing in Europe even when the odds are stacked against them.

The last-16 tie promises to be a chess match in which Antonio Conte’s chaotic style of management could be trumped by Pioli’s calmness, with the Milan boss a master at controlling games with his intelligence. 

Rodrigo Bentancur’s absence is a colossal blow for Spurs, and their problems in midfield are under the magnifying glass of Milan who want to impose their football in the middle of the park.

How will Milan approach the game?

Despite their difficulties, Milan remain a tricky team to face due to their winning DNA – only Real Madrid have more European Cups – and Spurs will have to be very careful.

Captain Davide Calabria should return to the starting XI on Tuesday after being benched against Torino: a way to guarantee rest for the young full-back so that he is 100 per cent ready for the European clash.

Sando Tonali will have a crucial role to play in central midfield, with Ismael Bennacer still not quite fit enough to return to action. while Theo Hernandez delivered an improved display against Torino, and could pose a threat down the left flank.

Ismael Bennacer (pictured) will miss the first leg as he continues his recovery from injury

Pioli may look to challenge Tottenham by matching Antonio Conte’s 3-4-2-1 formation

Milan could then match up with Tottenham tactically by playing the 3-4-2-1 formation often deployed by Conte, with Brahim Diaz and Rafael Leao in support of the evergreen Olivier Giroud.

Italian football remains heavily reliant on tactical nous, and Pioli could look to use this to his advantage against Conte’s side. By using the same system and closing the gaps on the pitch, this should lead to fewer defensive risks, giving Milan their best chance of overcoming their Premier League opponents.

What’s happened to Origi and Tomori?

Both Divock Origi and Fikayo Tomori have fallen short of expectations this season, and have suffered terribly during Milan’s most difficult period of the campaign as the club have fallen out of the title race and into a battle to make the top four.

Origi’s return of two goals in 15 Serie A matches is a poor one, and he has not contributed anywhere near enough for a player that was expected to move above Giroud and Zlatan Ibrahimovic in the pecking order. 

Origi is currently a back-up option who is too expensive and has little impact on the pitch.

Milan fans dreamed of having found Jon Dahl Tomasson’s heir, the striker who helped the side to domestic and European glory in the early 2000s. Instead, they have had to settle for a clone of Javi Moreno, whose brief spell in Milan was a disaster and led to him being replaced by Tomasson.

Divock Origi (right) has scored just two goals since he joined Milan on a free transfer last summer, while Fikayo Tomori was one of Serie A’s best defenders last season, but hasn’t been this term

Meanwhile, Tomori was vital to Milan’s title triumph last year, but has fallen away considerably this term.

He picked up a hip injury last month that has kept him out of the team in recent weeks, and it is difficult to imagine him being 100 per cent fit to take on Tottenham on Tuesday.

Matteo Gabbia and Simon Kjaer have wasted the opportunities handed to them by Pioli in Tomori’s absence, and this could lead to the Italian coach going with an inexperienced back three of Pierre Kalulu, Malick Thiaw and the returning Tomori for one of Milan’s biggest games of the season.

Giroud to stake his claim for another year in Milan

Giroud is an idol of the Milan fans and will sign a 12-month contract extension by the end of March. 

He has become the figurehead of the team, and will continue in this role as Zlatan Ibrahimovic ends his career at the end of the season, although the Swede is expected to remain within the club in some capacity, according to Gazzetta dello Sport. 

There are still a few minor details to be ironed out before Giroud signs on the dotted line.

But an agreement is likely to be reached, and this could be helped by the bonuses that the Frenchman will pick up if Milan get past Tottenham and advance to the quarter-finals of the Champions League, as reported by Corriere della Sera.

Olivier Giroud is set to stay at Milan for another year, and has been one of their better players

Tottenham must test Tatarusanu

If Spurs want to get a positive away result against Milan they will have to focus on the team’s weak point: goalkeeper Ciprian Tatarusanu. 

The Romanian shot-stopper has taken the gloves at the San Siro due to an incredible series of unfortunate situations, with Mike Maignan out since September thanks to a calf problem, Antonio Mirante struggling physically, and the club waiting for new signing Devis Vasquez. 

In a brief interview with DAZN, Milan’s technical director Paolo Maldini delivered an update on Maignan’s injury, revealing: ‘Mike should be available in 10 days. A goalkeeper who hasn’t played for so long has to keep his distance. Having had two relapses he has to be careful.’

Maignan’s lengthy lay-off has made the defence less secure, with the backline clearly not having as much confidence in Tatarusanu. 

If Tottenham test the former Fiorentina goalkeeper regularly, they will have a good chance of forcing a mistake and getting on top in the tie.

Milan have badly missed Mike Maignan who has missed most of the season with a calf injury

Milan don’t run enough and lack intensity

Milan have had a problem with their physicality in the second phase of the season, as confirmed by Opta’s depressing numbers. 

Captain Calabria leads a tired team on the pitch that currently occupies 14th in Serie A for distance covered in matches, but it is their lack of intensity that has become a major concern. 

Kalulu and Tomori are no longer leading the way in terms of individual statistics, while Gabbia and Kjaer do not appear to possess the physical condition needed for a side that wanted to be challenging for the title once again.

The backline is not the only issue, as the midfielders seem to play in slow motion and miss many opportunities to add some much-needed pace to the team’s attacks. 

Switching formations midway through the season has also been difficult for some of the more established players who have struggled to find their best form since the turn of the year. 

Tonali and Hernandez unable to inspire Milan

Tonali blossomed as a player in Milan’s title-winning team last season, but has been unable to replicate those performance in the last six months. 

Sandro Tonali (pictured) has failed to hit the heights that he reached last season for Milan

The feeling is that the team doesn’t have the strength to protect the defence, and this has been caused by the physical and mental decline of its main players. 

Even Hernandez is unrecognisable, perhaps due to the stress of the World Cup and the disappointment of losing the final to Argentina.

The whole team struggles to play with intensity, but these two players have disappointed fans the most with their drop-off in performances. 

Milan are below their bitter rivals Inter in the table, and that is a reflection of the mismanagement of the squad by Pioli.

The side are suffering physically, and it is Pioli and his staff that have to take responsibility for Milan’s negative start to 2023.

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