Tottenham vs Milan: Champions League Preview, Lineups & Prediction

Tottenham Hotspur host Milan at the Tottenham Hotspur Stadium on Wednesday night as they aim to overturn a 1-0 first leg deficit in their round of 16 Champions League tie. Brahim Diaz scored the only goal at the San Siro last month as Stefano Pioli’s side recorded a narrow win but all is still to play for as Milan travel to North London.

After a woeful return to action following the World Cup break, Milan recorded just one victory in eight matches in all competitions. However, starting with a 1-0 home triumph over Torino, the Rossoneri looked to get things back on track. Another three wins would follow, meaning that Pioli’s men had recorded four consecutive victories and had failed to concede in either of them.

However, the inconsistency returned and a dismal 2-1 defeat away to Fiorentina at the weekend brought them back down to reality. Milan now sit outside the top four and are a behemoth 18 points behind league leaders Napoli.

A similar situation has unfolded at Spurs too and they are just about still clinging on to their fourth spot in the Premier League. However, Liverpool are hot on their tails as they look set up for a promising end to their campaign.

Antonio Conte has been absent from coaching his side now for the past four matches after undergoing gallbladder surgery last month. Nevertheless, the big news is that the former Juventus and Inter coach will return for the crucial second leg matchup on Wednesday. His presence will offer a big boost down on the touchline for his side, despite not being able to invoke much in the first leg when he was present at the San Siro.


Tottenham Hotspur

Having suffered just one defeat at the Group Stage, Spurs topped Group D ahead of Frankfurt, Sporting CP and Marseille. Tottenham were also undefeated at home in their group, registering wins over Marseille and Frankfurt, before drawing 1-1 with Sporting in their penultimate fixture.

You have to go all the way back to October 2019 until the last time Tottenham suffered a defeat at home in the Champions League, although, that was a 7-2 rout at the hands of Robert Lewandowski and Bayern Munich. Spurs are on a five-match unbeaten run in the Champions League at the Tottenham Hotspur stadium but it looks a little more impressive since they failed to qualify for the competition for two seasons between 2019/20 and 2022/23.

Conte’s men will also take confidence in the fact that they have won all three of their last home fixtures as well, picking up victories over Manchester City, West Ham United and Chelsea respectively. Nevertheless, Tottenham have also lost twice at home already this year, suffering defeats to Aston Villa and North London rivals Arsenal.

Player to Watch: Harry Kane 

Harry Kane is the obvious choice as Tottenham’s player to watch but that’s because they have very little else going for them up top at the moment and they need goals. Heung-Min Son has struggled all season and has just five league goals all campaign. Kane will need to return to form in Europe, however, since he has scored just one goal during this season’s Champions League campaign.


A switch to a three-man defense, consisting largely of Pierre Kalulu, Malick Thiaw and Fikayo Tomori, has helped sure up the backline. The return of Mike Maignan in goal has also aided the defensive stability and he made his first appearance for the first time since September against Atalanta at the end of February.

However, the defense looked woeful against Fiorentina at the weekend with all three centre-backs showing some worrying signs. Tomori looked careless in possession and gave away a penalty kick for the opener, Thiaw was booked for a rash challenge on the edge of the box and Kalulu was far from his best over towards the right-hand side.

History is also not on Milan’s side either and they failed to get past Spurs when the two sides last met back in 2011. Nevertheless, if a repeat of the away leg stands this time around – 0-0 – the Rossoneri will be delighted since that is all they need to secure a spot in the quarter-finals. That certainly seems feasible as well since Tottenham have failed to score in either of their last two matches.

Player to Watch: Theo Hernandez

The Frenchman has been on excellent form for Milan and was unfortunate not to be credited the opening goal against Atalanta after his fierce strike rebounded off the post and onto goalkeeper Juan Musso before crossing the line. Hernandez scored with a fantastic finish against the Viola at the weekend though, despite it only being a consolation.

Team News

Tottenham will continue to be without key players Hugo Lloris and Rodrigo Bentancur as they continue their recovery from serious injury. However, they will also be without Yves Bissouma and Ryan Sessegnon are also missing due to injury. Eric Dier is suspended for the match here as well after picking up a yellow card in the first leg, leaving the Spurs squad extremely thin.

There is positive news in the Milan camp, however, since both Olivier Giroud and Diaz have returned to training. The French striker had been a doubt since he was battling with illness, whilst Diaz was absent from the loss in Tuscany due to a knee problem.

Tottenham Hotspur vs Milan Potential Lineups

Tottenham Hotspur (3-4-2-1): Fraser Forster; Cristian Romero, Clement Lenglet, Ben Davies; Emerson Royal, Pierre-Emile Hojbjerg, Oliver Skipp, Ivan Perisic; Dejan Kulusevski, Heung-Min Son; Harry Kane

Milan (3-4-2-1): Mike Maignan; Pierre Kalulu, Malick Thiaw, Fikayo Tomori; Junior Messias, Sandro Tonali, Rade Krunic, Theo Hernandez; Rafael Leao, Brahim Diaz; Olivier Giroud

Tottenham Hotspur vs Milan Prediction

In one of the most intriguing ties in the Champions League last 16, Tottenham and Milan are set to play in a close encounter. It was a cagey affair at the San Siro that yielded slightly over two expected goals. Milan will be looking to protect their lead but will need a better defensive performance than at Fiorentina last time out.

Conte’s return offers a big boost for the hosts and Milan’s terrible away form doesn’t bode well for them heading into the second leg. The Tottenham Hotspur stadium will be rocking too and so that’s why we’re backing a slim Spurs victory on Wednesday.

Prediction: Spurs Win