Milan knocked Tottenham out of the Europe competition with a 1-0 aggregate score after a 0-0 draw in London.
Despite a delay due to traffic, Milan showed early aggression and had some good players like Brahim Diaz and Theo Hernandez.
They almost scored from a free-kick, but Junior Messias missed the target.
Tottenham, with Antonio Conte back, struggled to even the score and their best chance was when Emerson Royal’s shot was deflected.
Harry Kane, Heung-min Son, and Dejan Kulusevski underperformed and were jeered by fans at halftime.
Milan continued to press in the second half, with Diaz and Olivier Giroud testing Fraser Forster.
Spurs brought on Pedro Porro, but he couldn’t make a difference, and a Pierre-Emile Højbjerg attempt was saved by Mike Maignan.
Spurs’ situation worsened when Cristian Romero received a second yellow card and was sent off.
Drama ensued as Kane’s header was stopped by Maignan, and Divock Origi hit the post at the other end.
Milan advanced to the quarter-finals, while Tottenham’s pursuit of a trophy goes on.