Although an off day in the schedule, Monday was significant for Tottenham Hotspur, as the team’s UEFA Champions League future was set, with Spurs drawn against AC Milan.
There were two parts to the suspense of the Round of 16 draw on Monday. The first was the draw itself, and the second was the release of the fixture dates. With both complete, the next step for Tottenham in the Champions League journey is known.
Tottenham has a somewhat familiar foe
When Tottenham was drawn against AC Milan, it was like bringing back an old friend. Spurs have faced Milan four times previously in European competition (transfermarkt.com). For some fans, the match-up may harken back to an earlier time, where a Peter Crouch goal at the end of the first leg was enough to send Spurs through 1-0 on aggregate.
That 2010/11 match-up was the second European battle between the two clubs after Tottenham advanced over Milan in the 1972/73 UEFA Cup Semi-finals. That time Spurs won 3-2 on aggregate.
Juventus is the only Italian club Spurs have faced more often, having played six times, which will be the same for Milan after these upcoming games.
And while the club is somewhat familiar with Milan in terms of European history, coach Antonio Conte is far more familiar with the Italian side.
Conte knows Milan very well
In his career, Conte has coached over 570 matches. Across all those matches in different leagues, there is no team he has faced more often than AC Milan, who Conte has coached against 14 times (transfermarkt.com).
Milan also has the distinction of being the team Conte has beaten most often, with ten wins in his 14 matches against the Rossoneri. Although Conte does have a better points-per-match total against some other teams, with only one loss in 14 games, historically, Conte has had Milan’s number.
Of course, a coach and some successful history do not win games, but it is good to know that combined in 18 matches, the club and coach have 12 wins, five draws, and just one defeat against Milan.
When does Tottenham play in the Round of 16
Several hours after the draw, the actual fixture dates were released. Tottenham’s trip to Italy will be one of the first two matches of the round on Tuesday, 14 February 2023. Spurs then host Milan on Wednesday, 8 March 2023.
Overall, it was a good draw for Tottenham as they avoided PSG and will play a team Conte is familiar with.