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.

Milan had the first real chance of the match after 18 minutes with a free kick straight off the training ground. The ball was fed into the path of Junior Messias inside the box but the Brazilian could only drag his driven effort wide of the target. A big let off for Tottenham.

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. At the half time whistle, neither side had managed a shot on target.

Tottenham came out for the second half with much more intensity, playing almost exclusively in Milan's half but again without creating enough in attacking areas. Spurs tried time and time again to fire crosses into the box but too often the cross lacked quality - of the 26 they attempted, they completed just five.

After 64 minutes Tottenham had their first real opportunity, Pierre-Emile Hojbjerg did well to pull the ball to the side before firing in an effort which Mike Maignan had to tip over the bar and out for a corner.

Tottenham's night went from bad to worse when Cristian Romero was given a second yellow card 13 minutes from time for a late challenge to hinder the home side's late attempts.

The board went up for six minutes to a raucous reception and it was in stoppage time where Spurs had their best chance. Heung-Min Son fired in an excellent cross which Harry Kane was able to head goalward but Maignan was on hand to make a stunning save.

Tottenham will look back on tonight as a real missed opportunity, not purely for the fact that they were eliminated from the competition, but because of the manner that Spurs went out. In a match of such magnitude, of such high stakes, at home under the lights, it was a thoroughly underwhelming performance from a side who just couldn't seem to get going. Milan rarely looked threatened throughout and in truth, their players will probably be somewhat surprised at how straightforward tonight's match was. For Spurs and Antonio Conte, it's three matches without a win, three matches without scoring a goal and their last opportunity to win a trophy this season has now gone.

The AC Milan defender did all of his defensive work with confidence and assuredness. He was switched on throughout, sprinting across the back line at times to cut out loose passes and win the ball for his side. He made four clearances, blocked two shots and made three tackles. He very rarely put a foot wrong with the ball either, helping his side to play out of defence and up the pitch. A brilliant performance from the 25-year-old.

Tottenham Hotspur: Forster 7, Romero 5, Lenglet 7, Davies 7, Royal 6, Skipp 6, Hojbjerg 6, Perisic 6, Kulusevski 6, Son 6, Kane 6. Subs: Sanchez 6, Porro 6, Richarlison 6

AC Milan: Maignan 7, Tomori 9, Thiaw 7, Kalulu 7, Theo 8, Tonali 7, Krunic 7, Messias 7, Diaz 7, Leao 7, Giroud 6. Subs: Bennacer 7, Origi 6, Saelemaekers 6

18' BIG CHANCE FOR MILAN! AC Milan work a brilliant free kick from the training ground, Tonali finds Messias Jr in the box but the Brazilian can only drag his shot wide. He will be disappointed to not have made the goalkeeper work from that angle.

50' BIG SAVE FROM FORSTER! - That is the best chance of the game so far. Brahim Diaz bundles his way into the box before firing an effort on target which Forster saves. The 34-year-old spread himself really well to deny Diaz.

64' BIG CHANCE FOR SPURS! - That is Spurs' best chance of the game so far. Hojbjerg fires an effort on goal which Maignan saves and it's out for a corner. Spurs are really turning up the heat now.

77' RED CARD - TOTTENHAM HOTSPUR - Romero is shown a second yellow card for a lunge and he is sent off.

90+4 OFF THE POST! - Divick Origi sees his effort cannon off the post!

AC Milan are into the UEFA Champions League quarter final for the first time since 2011/12.