Tuesday marks the start of the Champions League knockout phase, with AC Milan hosting Tottenham Hotspur for the first leg of their last-16 match.

Milan picked up where they left off with a tight victory against Torino on Friday, while the guests must bounce back after being destroyed 4-1 by Leicester City the previous weekend.

Following a brutal seven-game losing streak, which includes losses to their fierce rivals Inter in both the league and the Italian Super Cup, AC Milan knew that only victory would do against Torino on Friday.

Despite being a seven-time European champion, Milan hasn’t played in the Champions League knockout round since being defeated 5-1 on aggregate by Atletico Madrid in the last 16 in the 2013-2014 campaign.

The defending Italian champions have lost at the last-16 stage in five of their previous six tournament appearances, including the 2011–12 campaign when they lost 1-0 on aggregate to Tottenham. Milan knows they will face a challenge to advance to the quarterfinals after losing all four of their matches against Spurs in competition.

In their most recent last-16 match, Spurs were humiliated 4-0 on aggregate by RB Leipzig, which included a dismal 3-0 loss in the away leg. However, that match occurred under Jose Mourinho’s management, not that of Antonio Conte, who may be looking forward to seeing an old rival.

If you’re a fan of Tottenham, you’ll be pleased to learn that Conte has a winning record against Tuesday’s opponents. In fact, eight of his last nine matches against Milan have ended in victories. His most recent away victory over the Rossoneri came in 2021 while he was in charge of Inter, the Rossoneri’s city rivals.

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