Official: AC Milan draw Tottenham Hotspur in Champions League last 16

AC Milan have been drawn against Tottenham Hotspur in the Champions League round of 16, the draw in Nyon confirmed today.

Milan secured their progression to the knockout stages of the competition for the first time since the 2013-14 season by beating Dinamo Zagreb home and away (3-1 and 4-0 respectively) and by routing Red Bull Salzburg 4-0 last Wednesday to seal second spot behind Chelsea.

The rules regarding not being able to draw a group winner from the same country (Napoli) or the winner of your own group (Chelsea) meant that Milan were able to face Manchester City, Spurs, Benfica, Porto, Bayern Munich or Real Madrid.

The first leg of the round of 16 tie will be played on February 14, 15, 21 or 22 at San Siro, and the second leg on March 7, 8, 14 or 15. Spurs will play at home in the second leg due to winning their group.

The last time that the two sides met in the competition was back in the 2010-11 season when the London club actually went through. Peter Crouch got the only goal of the tie as Spurs won 1-0 at San Siro in a feisty encounter, with the return game being a frustrating 0-0.