The 2022/23 Champions League campaign continues with a set of round-of-16 fixtures as Milan and Tottenham Hotspur go head-to-head on Tuesday night. Nine years since their last appearance in the competition’s knockout stages, the Rossoneri will be out to make amends for a woeful domestic season.
A decent return of three wins from six Group E matches (D1, L2) was enough to give Milan a runner-up spot behind Chelsea and fire them into the Champions League last-16 for the first time since 2013/14. While the die-hard San Siro faithful would say the Rossoneri are back to their natural habitat, it’s yet to be seen whether they have what it takes to make themselves comfortable in this environment again.
The seven-time European champions have experienced a false start to the new calendar year despite beating Serie A bottom-half strugglers Salernitana at the turn of 2023. Indeed, Stefano Pioli’s side had since gone winless in seven straight games in all competitions (D2, L5) before Olivier Giroud cut their misery last Friday.
The talismanic French striker headed home a second-half winner in Milan’s 1-0 home win over Torino, throwing under-fire manager Stefano Pioli a lifeline at the San Siro. Indeed, the club’s fall from grace in 2023 has cast doubt on the Scudetto-winning manager’s long-term future in Lombardy, with non-other than Tottenham boss Antonio Conte emerging as a potential candidate to fill his shoes at the end of the season.
Conte enjoyed resounding success against Milan throughout his trophy-laden managerial spells with Juventus and Inter, respectively. The esteemed tactician has racked up eight victories in nine encounters against the Rossoneri as a manager (L1) and will be looking to maintain that trend with Tottenham.
Preview
Milan
Milan’s memories of their last foray into the Champions League knockout stages are not quite fond, as they bowed out to Atletico Madrid in 2013/14 on an aggregate scoreline of 1-5. But while it’s hard to expect another heavy defeat here, the Rossoneri cannot take anything for granted after falling out of the Serie A top-four for the first time in two seasons.
With Pioli’s managerial future at Milan facing uncertainty, navigating a Champions League last-16 tie for the first time since 2011/12 could be a first step toward redemption. Unfortunately, the San Siro has been anything but a safe shelter for the Rossoneri in 2023, as they’ve picked up just one win in four competitive home outings this year (D1, L2).
Player to Watch: Olivier Giroud
Giroud’s role in Milan’s runner-up finish in Group E was critical. The veteran goal-getter tallied four goals and two assists in his six group-stage appearances, accounting for 50% of the Italians’ goal share in the group phase.
Tottenham Hotspur
Tottenham may have finished top of Group D, leaving Eintracht Frankfurt, Sporting Lisbon, and Olympique Marseille in their wake. Yet, their progression into the knockouts was hanging by a thread until the final group-stage matchday. After reaching the round of 16 for the first time since 2019/20, they’ll be looking to go one better and qualify for their first quarter-finals since 2018/19.
Playing Milan could come in handy, with Tottenham going unbeaten in all four previous European encounters (W2, D2). Spurs ousted the Rossoneri from this stage of the competition in 2010/11, as Peter Crouch scored the only goal to hand the Londoners a 1-0 aggregate triumph. However, the spirits in the visiting camp took a massive blow at the weekend. Despite opening the scoring, Tottenham suffered an embarrassing 4-1 Premier League defeat at Leicester City on Saturday.
Player to Watch: Harry Kane
He’s an obvious choice, isn’t he? However, despite leading the scoring club’s charts in the Premier League with 17 goals from 23 matches, Harry Kane massively underperformed in Europe. Although he started all six Champions League matches in the group stages, the Englishman netted just once, so he’ll be looking for a clean slate in springtime fixtures.
Team News
Injuries to several first-team regulars, including Mike Maignan, Fikayo Tomori, Zlatan Ibrahimovic, and Ismael Bennacer, will see Milan take the field severely weakened. That’s not the end of Pioli’s troubles, with Sergino Dest and Alessandro Florenzi also expected to remain on the sidelines.
On the other hand, Tottenham will be without first-choice goalkeeper Hugo Lloris due to a knee injury. Bit-part midfielder Yves Bissouma is also out of contention, with Conte still sweating over Rodrigo Bentancur’s fitness.
Milan vs Tottenham Hotspur Potential Lineups
AC Milan (3-4-2-1): Ciprian Tatarusanu; Pierre Kalulu, Simon Kjaer, Malick Thiaw; Theo Hernandez, Sandro Tonali, Rade Krunic, Davide Calabria; Rafael Leao, Brahim Diaz; Olivier Giroud.
Tottenham Hotspur (3-4-2-1): Fraser Forster; Ben Davies, Eric Dier, Cristian Romero; Ivan Perisic, Pierre-Emile Hojbjerg, Rodrigo Bentancur, Emerson Royal; Son Heung-min, Dejan Kulusevski; Harry Kane.
Milan vs Tottenham Prediction
Even a slender first-leg advantage could be pivotal to Milan’s bid to surpass Tottenham. But given the Italian champions’ rough patch in 2023, that might prove easier said than done.
The potential absence of Conte from Tottenham’s dugout may give Milan a helping hand, though, with the former Inter boss still recuperating from surgery. While he’s asked permission to attend this fixture, it’s still uncertain whether he was granted the approval.
Nevertheless, we expect a tight, keenly-contested midfield battle with only a handful of scoring chances. That’s where the Rossoneri should thrive, as we back them for success.
Prediction: Milan Win
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