AC Milan vs Tottenham Hotspur: Champions League Resumes With Intriguing Clash

• Seven-time European champions AC Milan finished as runners-up in Group E
• Tottenham Hotspur, runners-up in this competition in 2019, finished top of Group D
• Both teams will be looking to establish a first-leg advantage at the San Siro this week

AC Milan vs Tottenham Hotspur Odds

The odds for AC Milan vs Tottenham Hotspur have been taken from the DraftKings Sportsbook, where you can get a deposit bonus of up to $1000. 

AC Milan vs Tottenham Hotspur Pick

Back both teams to score and over 2.5 goals when AC Milan go head-to-head with Tottenham Hotspur in the first leg of this Champions League last-16 tie. 

AC Milan vs Tottenham Hotspur Predictions

Eighth Crown Unlikely but AC Milan Should Not Be Written Off

AC Milan are European soccer royalty. Only Real Madrid (14) have won more Champions Leagues than the Italian giants, who have been crowned kings of the continent on no fewer than seven occasions: in 1963, 1969, 1989, 1990, 1994, 2003 and 2007.

Despite their considerable pedigree in this competition, it has been some time since Milan were genuine contenders to win it. Since their last triumph 16 years ago, the Rossoneri have reached the quarter-finals just once - in 2012, when they were knocked out by Pep Guardiola’s Barcelona. 

Milan were entirely absent from the competition for seven straight seasons before they made their return last term. It did not go well: Stefano Pioli’s side amassed just four points and finished bottom of an admittedly difficult group containing Liverpool, Atletico Madrid and Porto.

Milan more than made up for the disappointment of that early exit by winning the Serie A title. It was a success that most observers of Italian soccer, as well as the best online sportsbooks, did not see coming. A season of transition had been anticipated, but Pioli did a brilliant job to get Milan over the line.

However, it is safe to say they will not be retaining the scudetto this time around. Milan are already 18 points adrift of runaway leaders Napoli, and are instead locked in a battle to finish in the top four. Pioli’s men beat Torino 1-0 on Friday, but before that they had lost three matches on the bounce in Serie A.

Milan are not among the favorites to win the Champions League, but both sides will see this as a winnable tie and a chance to reach the quarter-finals. The Rossoneri still have plenty to play for this season.

Inconsistent Spurs Unable to String Positive Results Together

Tottenham Hotspur began the 2022/23 campaign hoping to potentially challenge for the Premier League title, but like AC Milan there is no chance of them finishing on top of the pile from here. Spurs are instead involved in the race for a top-four finish, which would bring with it a place in next season’s edition of the Champions League.

It looked like Tottenham had turned a corner after an inconsistent run of form both before and after World Cup 2022. Back-to-back victories over Fulham and Manchester City boosted Spurs’ position in the standings, but Antonio Conte’s side were then thrashed 4-1 by Leicester City on Saturday - less than ideal preparation for their return to continental competition.

It was yet another example of Spurs following one step forward with two steps back. The 1-0 defeat of Manchester City had the potential to be a turning point in Tottenham’s season, but they failed to build on that impressive victory. 

It is not just that they lost to Leicester last time out, but the manner of the defeat was cause for concern as we approach the business end of the season. Spurs were all over the place defensively, and despite having their first-choice front three of Harry Kane, Son Heung-min and Dejan Kulusevski back together, they did not carry much of an attacking threat from open play.

Needless to say, a much improved display is required if Tottenham are to pick up a positive result at the San Siro on Tuesday. The problem for Spurs supporters is that it is so hard to know what you are going to get from Conte’s team.

Goals at Both Ends the Way to Go In Tuesday’s First Leg in Italy

When it rains, it pours. Just a day after their heavy loss at the King Power Stadium, Tottenham were hit with the news that star midfielder Rodrigo Bentancur looks set to miss the rest of the season after sustaining a knee injury in the defeat by Leicester. Spurs lack guile and creativity without the Uruguay international, so that is a serious blow.

Equally concerning for Conte is the way his side defended against Leicester. Cristian Romero was banned for that match but is available for selection on Tuesday, and his return to the backline could help to tighten things up.

Even so, Milan will fancy their chances of finding holes in Tottenham’s defensive structure. They have scored in 100 percent of their home games in Serie A this term, so the Premier League side will have their work cut out in trying to keep Milan’s attack quiet.

But there is reason to believe that Tottenham can find the back of the net too, not least because Milan have conceded an average of 2.6 goals per game in their last five encounters in all competitions. 

Goals are on the cards in this one - we recommend backing both teams to score and over 2.5 in total.

How to Watch AC Milan vs Tottenham Hotspur

• Teams: AC Milan vs Tottenham Hotspur
• Location: San Siro, Milan, Italy
• Time: Tuesday 14 February 2023, 3PM EST
• How To Watch: Paramount+