Cristian Romero sees red as Tottenham crash out against AC Milan in Champions League

AC Milan held Tottenham to a goalless draw in London and progressed to the UEFA Champions League quarter finals. Antonio Conte's side struggled to get into any sort of rhythm in the early part of the first half.

Ad Milan were the first to threaten, as Junior Messias received the ball following a clever free kick but could only drag his shot wide of the target. Champions League'Big mistake' — Hoddle says Spurs may have already missed ‘only’ trophy chance12 HOURS AGO Spurs grew into the first half around the 30 minute mark but still failed to show the required quality in the final third to really test Milan.

Tottenham came out for the second half with much more intensity, playing almost exclusively in Milan's half but again without creating enough. Cristian Romero was given a second yellow card and his marching orders 13 minutes from time for a late challenge to hinder the home side's late attempts.