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AC Milan vs Tottenham Hotspur Preview – Prediction, how to watch & potential line-ups

The highly anticipated Champions League knockout stage gets underway on Tuesday, as AC Milan and Tottenham Hotspur go head-to-head in their first leg round-of-16 tie. 

Despite making it out of the Champions League group phase for the first time since 2013/14, the reigning Serie A holders may not necessarily look forward to this fixture.

It’s been a troubling start to the new calendar year for the Rossoneri, with last Friday’s narrow 1-0 home league triumph over Torino halting an abysmal seven-game winless run in all competitions (D2, L5).

Olivier Giroud’s winner lifted Milan to fifth in the Serie A standings and potentially saved manager Stefano Pioli’s job for the time being amid growing speculation about his long-term future at the San Siro. 

Among the potential candidates on the Italians’ shortlist to replace the experienced tactician at the end of the season is reportedly non-other than Tottenham boss Antonio Conte.

During his previous managerial spells at Juventus and Inter Milan, Conte had a habit of tearing Milan apart, having won eight of his nine matches against the Rossoneri between 2013 and 2021 (L1).

His phenomenal personal H2H stats against the seven-time European champions sounds like a perfect recommendation for the job, yet they’ll stay on opposite sides in this tie.

After guiding Tottenham to the Champions League round of 16 for the first time since 2019/20, the esteemed manager will be looking to go one better and navigate their way into their first quarter-finals since 2018/19.

Match Preview

AC Milan

A paltry return of three wins from six Group E outings (D1, L2) proved enough to secure Milan a runner-up spot behind Chelsea and give them a berth in the Champions League knockouts for the first time in nine years.

However, problems often emerge in springtime European fixtures for the Rossoneri, as they’ve failed to score in nine of their last 14 games in the Champions League knockout stages.

If that’s not enough to further destabilise Pioli’s underperforming side, a four-game winless H2H record against Tottenham in major European competitions could do the trick (D2, L2). 

Tottenham Hotspur

Tottenham’s only previous encounters against Milan have come in the Champions League last-16, with Spurs winning their 2010/11 round-of-16 tie 1-0 on aggregate, courtesy of Peter Crouch’s goal.

Although Conte has yet to recover from surgery earlier this month, he insists on travelling with Tottenham to his home country following an underwhelming 4-1 Premier League loss at Leicester City last weekend.

Spurs’ underwhelming defeat at the King Power Stadium kept them outside the top four, putting the emphasis on winning this tie to restore morale among the north London faithful.  

AC Milan vs Tottenham Hotspur Potential Line-ups

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. 

How to Watch?

Milan vs Tottenham, alongside all other matches in Europe’s most prestigious club competition this season, is available to watch online via Champions League live streams.

AC Milan vs Tottenham Hotspur Prediction 

Milan’s glory days in European football are long gone, while the ongoing form and injury crisis at the San Siro threatens to postpone their return to grace. 

We wouldn’t go as far as to back Tottenham to win the first leg in Italy, but we don’t expect the Rossoneri to do it either.

AC Milan 1-1 Tottenham Hotspur 

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