Despite only winning three games apiece during the group stage, AC Milan and Tottenham have advanced once more to the Round of 16 of the UEFA Champions League (UCL). Both teams have experienced domestic difficulties, but reigning Serie A champions and seven-time European champions Milan have been particularly troubled. Despite the excitement of making it through a UCL group stage for the first time in nine seasons, Milan is currently worried that their domestic struggles could prevent them from competing in Europe in 2023/24.

Although Milan ended their seven-game winless streak (D2, L5) across all competitions last Friday with a 1-0 Serie A victory over Torino that moved them up to fifth place, some journalists went so far as to speculate about the manager Stefano Pioli’s immediate future if his team fails to advance to the UCL quarterfinals and/or cannot qualify for the next one by finishing in the top four. In fact, several Italian tabloids even claimed that Milan’s ownership was going to contact Spurs manager Antonio Conte and another option after the season.

Despite being cautioned by assistant Cristian Stellini that “he needs to be careful” about his recovery from surgery after 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, Conte insists on traveling with his Tottenham team to his home country, where his family still resides. After Tottenham’s recent 1-0 PL victory over Manchester City, the former UCL champion—who won it as a player in 1995–1996—changed his mind on the team’s season, weeks after calling a top-four finish improbable.

Tottenham, who finished second in the UCL in 2018–19, advanced to this stage with seven points from their final three group stage games despite scoring and giving up goals in each of those games. The 2-1 victory in Marseille during that time would have been especially encouraging for this first leg as Spurs had only won three of their previous 13 UCL away games (D5, L5). Ironically, they advanced past the Round of 16 in their previous meeting with Milan in this tournament (2010–11) thanks to a first-leg victory at San Siro (1-0) and a 0-0 draw at White Hart Lane.

Players to keep an eye on: Olivier Giroud, Milan’s lone goal scorer from the weekend, has plenty of experience playing against Tottenham having scored four goals against them. He will have played in 19 more games versus Spurs than any other team by the time the game is through. Dejan Kulusevski of Tottenham has also faced Milan seven times, but has only had sporadic success (W1, D2, L4).
Five of Milan’s most recent UCL games have been decided by multiple goals (W3, L2).

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