Spurs trudged to a lifelife 0-0 draw to confirm their exit from the Champions League as AC Milan reached the quarter-finals for the first time in 11 years. The result was met with loud boos from the fans at the full-time whistle and throw further doubt on Antonio Conte's future.
Spurs failed to muster a meaningful attempt on target in the first half as their frustration boiled over with Conte booked for letting his emotions get the better of him. The subdued hosts were not helped by having defender Cristian Romero sent off for a second yellow card in the 78th minute.
Milan could have made it a more comfortable night had they taken a few of the good chances they created but in the end a masterclass of defensive game management saw them through. While Stefano Pioli's Milan can look forward with optimism, Tottenham's season is fizzling out after a dismal week in which they also lost in the FA Cup to second-tier Sheffield United and to Wolves in the Premier League.