AC Milan progressed to the quarter-finals of the Champions League for the first time since 2012 as the Italian champions held out for a 0-0 draw at 10-man Tottenham to win 1-0 on aggregate.
A European elimination hot on the heels of an exit from the FA Cup means Tottenham’s 15-year wait to win a trophy will extend for at least another season.
Antonio Conte’s return to the touchline failed to inspire a response from his side as Tottenham were toothless in attack and had to play the final 12 minutes a man down as Cristian Romero was sent off for two bookable offences.
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