AC Milan vs Tottenham Hotspur

AC Milan’s first foray into the Champions League round of 16 since the 2013/14 season pits them against Premier League top-four hopefuls Tottenham Hotspur at the Stadio San Siro.

Coming into the first leg of their first Champions League last-16 tie against Tottenham since an underwhelming 1-0 aggregate loss in 2010/11, AC Milan toppled Torino 1-0 at home in Serie A, ending a dismal run of seven winless matches in all competitions (D2, L5). Scudetto-winning manager Stefano Pioli has come under heavy scrutiny following Milan’s disappointing league start to the new calendar year, resulting in ‘I Rossoneri’ tumbling outside the Serie A top-four for the first time in two seasons. The reigning Italian champions will be keen to prove the abovementioned win over Torino was the beginning of their resurgence against a Tottenham side they’ve failed to beat in any of their four previous H2Hs in European football (D2, L2).

In the meantime, with Milan-linked manager Antonio Conte yet to recover from surgery, Tottenham Hotspur slipped to a disastrous 4-1 Premier League defeat at bottom-half Leicester City last weekend despite opening the scoring. ‘Spurs’ finished top of Group D, but their bid to reach the Champions League knockouts for the first time since 2019/20 was hanging by a thread until the final group-stage matchday. Conte has requested to travel with his Tottenham side to his home country, which could be a game-changer for the Londoners. Conte has racked up eight wins in his nine personal H2Hs against Milan as a manager (L1), so his presence in the dugout should bolster the visitors’ hopes of defying a topsy-turvy four-game form away from home (W2, L2).