In a dull Round of 16 second leg, AC Milan advanced to the quarterfinals 1-0 on aggregate, and Antonio Conte, who had been away from the club for five weeks, was unable to motivate Tottenham to a Champions League comeback.
After gallbladder surgery, Spurs manager Conte had a discouraging night as he witnessed his wasteful players exit the tournament when AC Milan's Brahim Diaz scored early in the first leg. Spurs' sorrow was only made worse by Cristian Romero's late dismissal for receiving a second yellow card.
Tottenham's unceremonious withdrawal from Europe makes it all but likely that they won't take home a trophy this year.
Tottenham had already lost to lower-league Sheffield United in the FA Cup, and Nottingham Forest eliminated them in the third round of the Carabao Cup. They are currently far behind Premier League leaders Arsenal by 18 points as well.
- Forster (GK)—Romero, Lenglet, Davies, and Spurs (3-4-3) — Emerson, Skipp, Hojbjerg, Perisic (53' Porro), Richarlison (70'). Son, Kane, and Kulusevski (D. Sanchez at 83')
- Maignan (GK) — Thiaw, Kalulu, Tomori — Hernandez, Tonali, Krunic, Messias (56' Saelemaekers) — Diaz (81' Bennacer), Leao (89' Relic), and Giroud (81' Origi) are the other members of AC Milan's (3-4-3) lineup.
In a lackluster effort, Tottenham had just one chance on goal before leading scorer Harry Kane's header from one of the few precise crosses the hosts generated in stoppage time was well stopped by AC Milan goalkeeper Mike Maignan.
Divock Origi, a former Liverpool striker, then nearly gave Milan breathing room as the guests took advantage of their desire to break. Despite Fraser Forster of Tottenham being beat, his shot struck a post.
The match was won by Milan, who nearly took the lead when Diaz's thunderous shot was turned away by Forster early in the second half.

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