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AC Milan vs. Tottenham Hotspur Preview: Could a Champions League run be in store?

For just the fifth time ever, Spurs enter the Champions League knockout phase.

Olympique de Marseille v Tottenham Hotspur: Group D - UEFA Champions League Photo by Jean Catuffe/Getty Images

With the club in its annual chase for fourth place, it sometimes takes a reminder that Tottenham Hotspur is actually still alive in the competition it constantly seeks to participate in. Form has ebbed and flowed this season, but Spurs are one of 16 clubs still alive in the Champions League, a fact that bears repeating.

When the Round of 16 draw occurred, it felt that Tottenham was at least a little fortunate to get AC Milan, despite its Italian title last season. That belief is even truer now, with the club coming into the tie in quite dreadful form, owning a 2-2-5 record since returning from the World Cup.

Spurs have been far from unbeatable themselves, but do enter as the favorites to advance to the quarterfinals. A draw on Tuesday would be passable, especially with the suddenly alarming number of injuries, but there is every opportunity to take a lead back to North London. Enjoy the ride — to see this club compete in the knockout phase is still such a treat.

AC Milan vs. Tottenham Hotspur (Round of 16, 1st leg)

Date: Tuesday, February 14
Time: 3:00 pm ET, 8:00 pm UK
Location: San Siro, Milan, Italy
TV: Paramount+ (USA), BT Sport 1

How we got here: Spurs topped their group with 11 points, thanks to a buzzer beater from Pierre-Emile Hojbjerg on the final day in Marseille. Meanwhile, Milan took 10 points in its group, finishing second to Chelsea; the Blues took six points in the two head-to-head fixtures, with Milan going 3-1-0 otherwise.

Of course, this particular tie will bring back memories of 2011, which was the club’s first knockout round appearance. Since then, Tottenham has made three more trips to this stage of the competition (with varying levels of success), and Tuesday brings about journey number five, the first since Leipzig in 2020. It has been nearly 10 years since the home side has advanced this far in the Champions League, so both sides will be full of eagerness.

Recent results:

  • Feb 2011: 0-1 win, away — R16, 1st leg (Crouch)
  • Mar 2011: 0-0 draw, home — R16, 2nd leg

Spurs should feel good about their odds, with Milan struggling badly in 2023 and the second leg to be played at home next month. However, it will not be so straightforward with Hugo Lloris set to miss both contests, Rodrigo Bentancur now out for the season, Yves Bissouma injured as well, and Hojbjerg forced to miss Tuesday thanks to yellow card accumulation.

That is a lot of names to be absent in midfield, and memories of a Harry Winks-Moussa Sissoko pairing suddenly feel rosier compared to whomever Antonio Conte and Cristian Stellini elect to deploy at the San Siro. Whatever the starting XI ends up being is going to need the big-name players to step up and perform under the sport’s brightest lights.

Defense has been a problem for Milan, conceding 15 goals in seven Serie A matches since the break. Spurs must find a way to capitalize and take advantage of this opportunity and certainly have the personnel to do so. Progressing the ball may continue to be a challenge, but this is no time to play tight. This is what football is all about, and Tottenham has a prime chance to make some more classic memories in this illustrious competition.