Tottenham Hotspur's Champions League campaign ended in bitterly disappointing fashion as they failed to overturn a first-leg deficit in the last 16 against AC Milan.
Spurs paid the price for another passive start that allowed Milan to settle into their task - the misery complete when defender Cristian Romero was sent off late on after receiving a second yellow card for a wild challenge on Theo Hernandez.
Pierre-Emile Hojbjerg tested AC Milan keeper Mike Maignan with a powerful second-half shot and Harry Kane headed wide, but Spurs failed to mount sustained pressure on the Italian defence.
A late Kane header was brilliantly kept out by Maignan before Divock Origi struck the post for the visitors as Spurs went out tamely, their season now resting on the battle for a top-four place in the Premier League.