Champions League

UEFA Champions League Round of 16 Preview: AC Milan vs Tottenham Hotspur

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The 2022/23 UEFA Champions League took a hiatus in early November, shortly before the start of the World Cup and there has been a lull for more than two months now. The Champions League, inarguably Europe’s greatest competition returns to almost half a billion viewers and millions of screens in less than a month from now.

A tournament which never fails to deliver, the Champions League has always been full of surprises and no doubt, this current spell is no exception.

So far in this edition of the Champions League, the back of the net has been found 304 times in 96 matches, averaging 3.17 goals per game, with Paris Saint Germain’s Kylian Mbappe and Liverpool’s Mohamed Salah sitting at the top of the goalscoring charts with seven goals each.

On the back of a quite interesting Round of 16 draw in November, the entire football universe is set to experience some sensational match-ups in February and March. A couple of heavyweight fixtures have been thrown up for this round of Europe’s most illustrious tournament.

Defending champions and 14-time winners, Real Madrid, are heavily in the mix, as they look to add the quinzième UEFA Champions League to their trophy gallery in either Real Madrid City or the Santiago Bernabeu when they take on Jurgen Klopp’s Liverpool, a remake of the 2022 final in Saint-Denis.

This series will look at the next round of matchups!

Chelsea vs Borussia Dortmund

Club Brugge vs Benfica

Eintrach Frankfurt vs SSC Napoli

Inter Milan vs Porto

PSG vs Bayern Munich

RB Leipzig vs Manchester City

Real Madrid vs Liverpool

AC Milan vs Tottenham Hotspur

The sixth feature on this list is a tantalizing battle between the San Siro residents and the North Londoners. AC Milan take on Tottenham Hotspur in yet another amazing feature which promises to deliver. Rossoneri host The Lily Whites on Valentine’s before taking the return trip to the Tottenham Hotspur Stadium.

Which London club will finish highest in the table?







Milan qualified as runners-up behind group leaders, Chelsea, with 10 points, ahead of Salzburg and Dinamo Zagreb while Tottenham Hotspur didn’t have to overextend themselves in order to top Frankfurt, Marseille and Sporting Lisbon.

AC Milan

Stefano Pioli’s side are in the Round of 16 for the first time since the 2013-14 season when they faced eventual runners up, Atletico Madrid in the same stage and like their city rivals, Rossoneri would be hoping their days of Champions League glory are gradually coming back.

Milan are seven time winners of the prestigious Champions League, and their record is only bettered by the incredible 14-time Champions, Real Madrid. Milan have a lot of wonderful history when it comes to the UEFA Champions League and after a couple of seasons of wallowing in second-tier European football and being completely outside the picture, they’re back in the knock-out stages. But one opponent stands between them and qualification to the next round.

Tottenham Hotspur

Ever since Harry Kane, Hugo Lloris and the likes started plying their trade for the West London side, Tottenham have never reached the last eight of the Champions League. Infact, it’s safe to say no single player in the Tottenham squad has played a Champions League quarter final match as a Lily-white, their last quarter final appearance coming in 2010-11 against Real Madrid.

Spurs are no strangers to Italian opposition, then under Mauricio Pochettino’s management, the English club encountered Juventus in the 2017-18 Round of 16 of this competition. Spurs squandered a first leg advantage, conceding a 2-1 defeat on home ground to get knocked out. As recently as 2020, Tottenham were trounced 4-0 on aggregate by RB Leipzig at this same stage.

Apparently, making it to the final eight has been no easy task for Tottenham in recent times. But can that change with Milan?


Tottenham have never lost a tie to the Italians, never in their history. Having faced on four occasions, Spurs have a 50% win record(twice 2-1 and 1-0) and a 50% draw record(1-1 and 0-0)

Players to watch for:

Tottenham (Harry Kane)

As usual, Harry Kane spearheads the Tottenham attack and quest for goals. The Spurs forward will inarguably have the biggest chunk of work to do when they slug it out with the Italians in few weeks time. Even though he’s scored only two in the Champions League so far this season, Harry Kane still has his knack for scoring goals in the Premier League this season with 15 goals in 20 appearances.

He’s only being eclipsed by Erling Haaland as the goalscoring machine of the Premier League and in the race for the Golden boot. Spurs need his kind of attacking prowess in play when they face one of the biggest tests of their season.

Oliver Giroud(AC Milan)

The French international would be playing the same kind of role Kane would on the night as his team look to secure a spot in the last eight. Giroud has scored nine goals(four in the Champions League) and made six assists this season.

While it’s not outrightly superb, it’s the second highest number of goal contributions(15); after Rafael Leao(17) for Milan this season. Giroud can be a really clinical finisher on a typical evening so he’s much needed for this battle.

Rafael Leao(AC Milan)

The player with the highest number of goal contributions for Milan this season (17), Rafael Leao has what it takes to cause Tottenham a real upset, talk about size, pace, dribble, agility and finishing. The 23-year old Portuguese turned on the heat a couple of times in the 2022 World Cup especially speaking of his late curler against Switzerland which piled on the Swiss’ misery. The lad’s got great style and it’s hoped his features come in handy in this fixture.

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Jesuyemi is an avid fan of sports, especially football. He also enjoys WWE and athletics. He's been writing for a few years now and is a supporter of FC Barcelona.

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