Tottenham face a season-defining clash this evening (Wednesday) as they take on AC Milan in the Champions League last-16. Spurs are a goal down from the first leg and will be hoping to emulate the European turnaround achieved by London rivals Chelsea on Tuesday who secured a spot in the quarter-finals with a 2-1 aggregate win over Borussia Dortmund.
Optimism over that being achieved is not very high though as the seven days prior to their Champions League second leg have not been positive in the slightest. Last Wednesday, Spurs were knocked out of the FA Cup by Sheffield United and suffered a huge blow to their top four ambitions over the weekend, losing to Wolves after a late goal from Adama Traore. But Spurs can place that behind them with a victory at the Tottenham Hotspur Stadium against Milan.
The clash will also see the return of Antonio Conte who had spent the last two and a half weeks back recovering in Italy after undergoing emergency gall bladder removal surgery in early February. The Spurs boss returned to London on Sunday and conducted his first pre-match press conference since February 14, on Tuesday.
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"Yesterday (Monday) was positive and my feeling was really, really good," Conte said when he asked how he felt being back. "You know the importance for me to work with my players, to stay together and work with the staff and prepare for the game. From afar, I tried to stay very close to my staff and the players with the video and try to be linked.
"But, you know well, to be present is totally different. Totally different. I have to thank the whole staff, did a great job. Also, it wasn’t easy for the players to be three weeks without their coach. I know this."
Preparations for Milan have been slightly clouded by talk of Conte preparing to leave the club when his contract expires at the end of the season. There is an option to extend his stay by another 12 months, but it was one that would have to be mutually agreed upon by both parties.
Several reports have emerged recently that certainly hint towards an exit for the Italian. The Times report Conte's break from Tottenham in Italy has only strengthened his will to return to his home country at the end of his contract.
The Tottenham squad are also said to be anticipating an exit for Conte at the end of the season, as reported by the Athletic. They also claim that Mauricio Pochettino, Thomas Tuchel, Roberto De Zerbi, Marco Silva, Thomas Frank and Steve Cooper have all been named on a potential next manager shortlist.
To Spurs fans the most enticing name on that list is Pochettino. The Argentine spent five seasons in north London providing the club with some of the best memories in the 21st century including a Champions League final appearance. A poor start to the 2019/20 season saw him dismissed from his role at the helm of the club, but he could soon make a sensational return.
Three managers have been in place since he was sacked and all have struggled to achieve success at the club with Conte now relying on the Champions League, a competition he notoriously struggles in, to win silverware this season.
Tottenham's run under Pochettino to the final in 2019 was truly remarkable and Spurs' pre-match graphic would have likely got supporters thinking about him once again. One of the pre-prepared matchday graphics was revealed on Reddit and showed Harry Kane, Richarlison, Dejan Kulusevski and Son Heung-min all pictured.
All four of Tottenham's main attackers starting is highly unlikely as Conte likes to adopt a three-man forward line and playing a back five with those four options would likely be impossible. Under Pochettino however, all four playing would have certainly been an option.
Playing a 4-2-3-1, Pochettino's favoured formation, Son and Kulusevski would be on the wings with Kane deployed behind Richarlison. It certainly could be a possibility next season if Pochettino completes a sensational return with the Times also reporting he would be open to coming back to the club.
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