Kick-off on 14.02.23 22:00.

The Rossoneri secured their spot in the round of 16 only in the last round. The Devils finished second in Group E (ten points). The Lombardy team achieved victories at their home ground against Zagreb's Dinamo 3-1 and Salzburg 4-0, but suffered a 0-2 loss to Chelsea. The Spurs maintained their leadership in Group D (eleven points). The Lilywhites were defeated by Sporting in Lisbon 0-2, played a goalless draw against Eintracht in Frankfurt, and won against Marseille at the Vélodrome 2-1. The Milan vs. Tottenham clash can be watched online, and the sides have met twice before in European competitions at San Siro. In the semi-final of the UEFA Cup 1971/72, the opponents couldn't determine the winner, resulting in a 1-1 draw. Twelve years ago, the teams faced each other at the same stage in the Champions League. The London club secured a late victory in that match, ending with a score of 1-0. In the current tournament, Giroud has been involved in six goals for the Italian giants (four goals, two assists), while Leão contributed to three (1+2). The Serie A champions have reached the playoff stage for the first time since the 2013/14 campaign.

Since the early 2000s, the Rossoneri have participated in the round of 16 ten times and have been eliminated five times. In the 2007/08 season, the team couldn't progress against Arsenal (0-0, 0-2), and two years later, they were defeated by Manchester United (2-3, 0-4). In the 2010/11 campaign, the red and black team were unable to advance past Tottenham (0-0, 0-1), and in the 2012/13 competition, they were eliminated by Barcelona (2-0, 0-4).

Kane and Hojbjerg accumulated three points through goals and assists in the group stage (1+2), while Perišić provided three assists. In the 2013/14 Champions League, the Devils were defeated by Atletico (0-1, 0-4). Watch the Milan vs. Tottenham match online.

The Spurs made their debut in the tournament in the 1961/62 season and reached the round of 16 for the first time, eliminating Feyenoord (3-1, 1-1). In the 2010/11 campaign, the Lilywhites knocked out Milan at this stage, but in the 2017/18 season, they were unable to progress past Juventus (2-2, 1-2). In the following two years, Tottenham again reached the playoff stage, defeating Dortmund (3-0, 1-0) and losing to Leipzig (0-1, 0-3). Watch the Milan vs. Tottenham game online.