AC Milan and Tottenham make a return to the UEFA Champions League (UCL) Round of 16 despite winning just three group stage games each. Both sides have had their troubles domestically, especially reigning Serie A title holders and seven time European champions Milan, who despite the highs of qualifying through a UCL group stage for the first time in nine seasons, now have some ongoing concern about a potential lack of presence in Europe in 2023/24 due to their domestic form.
Although Milan ended their seven-game winless run (D2, L5) across all competitions with a 1-0 Serie A victory against Torino last Friday that took them up to fifth place, some journalists went as far as to speculate about the short-term future of manager Stefano Pioli if his side fail to reach the quarter-finals of the UCL, and/or cannot qualify for the next one courtesy of a top-four finish. In fact, some Italian publications even reported that Spurs boss Antonio Conte was on a two-man shortlist to be approached at the end of the season by Milan’s ownership.
Conte insists on travelling with his Tottenham side to his home country, where his family continues to live, despite being warned by assistant Cristian Stellini that “he needs to be careful” about his recovery from surgery following what would have been a stressful 4-1 Premier League loss to Leicester at the weekend that kept Spurs outside of the PL‘s top four. The one-time UCL winner (as a player in 1995/96) had previously changed his tune about Tottenham’s season following their recent 1-0 PL win against Manchester City, weeks after describing a top-four finish as unrealistic.
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Tottenham, UCL runners-up in 2018/19, stormed into this stage with seven points from their last three group stage games, scoring and conceding in all three matches, and the 2-1 win in Marseille during that period would have been especially encouraging as far as this first leg is concerned as Spurs had won just three of their 13 prior UCL away trips (D5, L5). Ironically, their last meeting with Milan in this competition (2010/11) saw them progress through the Round of 16 with a first leg win at San Siro (1-0) prior to a scoreless draw at White Hart Lane.
Players to watch: Milan’s only goalscorer from the weekend, Olivier Giroud, has netted four times against Tottenham and has a wealth of experience against them. At full-time, he will have notched up more games against Spurs (19) than any other club. Similarly, Tottenham’s Dejan Kulusevski has already taken on Milan seven times – but with very limited success (W1, D2, L4)!
Hot streak: Milan’s last five UCL fixtures were decided by a multiple goal margin (W3, L2).
Probabilities
| AC Milan (53.7%) | Draw (21.6) | Tottenham (24.7%) |
Prediction
| AC Milan 2-1 Tottenham |
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 Round of 16 despite winning just three group stage games each. Both sides have had their troubles domestically, especially reigning Serie A title holders and seven time European champions Milan, who despite the highs of qualifying through a UCL group stage for the first time in nine seasons, now have some ongoing concern about a potential lack of presence in Europe in 2023/24 due to their domestic form.){kind=link}