Today marks the start of the Champions League knockout phase, with AC Milan hosting Tottenham Hotspur for the first leg of their last-16 match. Milan picked up where they left off with a tight victory against Torino on Friday, while the guests must bounce back after being destroyed 4-1 by Leicester City the previous weekend. Olivier Giroud scored just after the hour mark to lead Milan to only their second victory of 2023. The Rossoneri had only been eliminated from the Coppa Italia by Ivan Juric's team last month, but they exacted retribution. An unconvincing but precious victory helps alleviate some of the pressure that had been building on Stefano Pioli, but with his side 18 points adrift of league leaders Napoli and out of the domestic cup, the Milan boss needs a positive performance form his side in the Champions League. Although Milan are seven-time European champions, Tuesday's meeting with Tottenham will represent the club's first Champions League knockout round tie since they were beaten 5-1 on aggregate by Atletico Madrid in the last-16 in the 2013-2014 season. The reigning Italian champions have been eliminated at the last-16 stage in five of their previous six appearances in the competition - including the 2011-12 campaign when they lost 1-0 on aggregate to Tottenham - and having failed to win any of their four competitive meetings with Spurs, Milan know that they will have their work cut out to progress to the quarter-finals.

When Rodrigo Bentancur gave Tottenham the lead in Saturday's away game against Leicester, Antonio Conte's return to the sidelines after recovering from gallbladder surgery appeared set to coincide with a successful outcome. However, it ended up being a forgettable afternoon for the North London club. Spurs suffered a crushing 4-1 loss as goals from Nampalys Mendy, James Maddison, Kelechi Iheanacho, and Harvey Barnes made their 1-0 victory against Premier League champions Manchester City seem like a distant memory. Tottenham must now get back up and dust themselves off if they want to repeat their historic run to the Champions League final from the 2018–19 season, which was led by Mauricio Pochettino. They won't want to revisit the memories of their most recent last-16 appearance, in which they were humiliated 4-0 on aggregate by RB Leipzig, including a dismal 3-0 loss in the away leg. However, that game was under Jose Mourinho's supervision, not Conte, who may be looking forward to a rematch with an old foe. If you're a fan of Tottenham, you'll be pleased to learn that Conte has a winning record against Tuesday's opponents. In fact, eight of his last nine matches against Milan have ended in victories. His most recent away victory over the Rossoneri came in 2021 while he was in charge of Inter, the Rossoneri's city rivals.

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