HIGHLIGHTS: TOTTENHAM - AC MILAN | CHAMPIONS LEAGUE 22/23

Both sets of players wearing black armbands tonight after the passing of Italo Galbiati, Fabio Capello's former assistant at the San Siro. And he's cost himself a buck in there early on in the game and he's got to be very careful now for the rest of the game. Talked about this pace that AC Milan have got, they'll look to exploit that now down the sides of Cristian Romero. Olivier Giroud, tatting it to Tonali. And then out wide, a chance for Junior Macias. Well he should have hit the target. It was well crafted. What a great opportunity for AC Milan, straight off the training ground. Giroud's ball there initially to Tonali wasn't great but he finds it down the right-hand side and it was a great opportunity, Macias. Kielisewski. Emerson Roy out. He's made a good run. Harry Kane takes over. A little deflection, almost wrong-footed the goalkeeper. Harry Kane goes to put it across and it's just the deflection that could have caused Mignon a little bit of an embarrassment. That was meant to go across the face of the goal. Kielisewski, trying to power away from Theo Hernandez. It's a mistake by Theo. And he's got out of jail, thanks to his team-mate Kalulu. Hernandez. Raheem Diaz. Junior Macias is making a run. Olivier Giroud waiting in the centre. Diaz gets the second bite at it. And maybe a third. Big save by Fraser Forster. He might just have kept Tottenham in the Champions League. Theo Hernandez. Raphael Layal. Flash through that six-yard box. Well if Tottenham didn't have enough warning signs in the first half, here's another reminder. Diaz once again finding himself in great space. Gets to the Spurs defence. A little bit lucky towards the end. But you credit Fraser Forster because he stands up, he makes himself big. That's a massive save at this stage of the game for Tottenham. Pedro Porro, trying to switch the play out to Son on the far touchline. Taken down well by the South Korean. Kane is waiting in the centre. Aiming towards him. The men have got six or seven red and black shirts back already. Another turnover. Pedro Porro finds Kulisiewski. Who finds Kane. He's trying to turn away from Tomori. He's stuck to his task brilliantly again. Comes back to Hoivier. Encouraged to shoot. Still going, Hoivier! It's the first real save that Mignolet's had to make. He does really well there, Hoivier. Kane gets half a shot away. The ball comes to him. He can't get away from Diaz there. But he makes some space for himself. Gets around Hernandez. And gets a shot away. Doesn't trouble the goalkeeper. But it shows intent from Tottenham. Gives the fans a lift. Gives the crowd a lift. Kept in by Theo Hernandez. That was a strong challenge. And it's going to be trouble here. It's a yellow card. I think that's Cristian Romero on the ground, if it is. He's going to be in big trouble. And he is going to be sent off. He's flown into a tackle there on Hernandez. It didn't really look like he needed to do that. There's confirmation. Yellow and then red. Tottenham Hotspur are going to spend the last 12 minutes plus injury time. And possibly, if they were to even get themselves back into this game, extra time with one less player. Davis looking for Kane. Salamekas. Kane again. And he's gone down, drawing the frow from Pierre Kouloulou. Clever hurry, Kane. He knows the challenge is coming in from Kouloulou. He puts his body between ball and player. Goes over, as we see him do so often. Well, it'll be an inspired substitution if Devincen Sanchez could score from this set piece. And it's his 200th appearance for Spurs. And he's wandered into that middle of the penalty area. Delivery wasn't perfect. Kane. Son. Devincen Sanchez goes over looking to win a penalty. The referee has played on and Raphael Liao is escaping. And Son is there for company. And Raphael Liao is testing the pace at the back line. He's gone beyond Skitt. It's found its way to Tonali. And it was blocked by Pedro Porro who got back in the nick of time. This is the claim for a penalty. Any legitimacy to it? No, I think he just gets there first. Devincen Sanchez, they just collide. I don't think there's any kind of collision with their feet. Hojbjerg. Tucked down by Malik Teow. And that's going to be a yellow card. I think he'll probably take that at this stage. It's a sacrifice worth making. Son to deliver. Spurs fans praying for time. It's Son into the box. It's Harry Kane. It's saved by Mignon. And what a massive stop that is. Tottenham's talisman denied. And now Milan come on the break. Origi is in the attack. He's joined now. Origi to finish it. He hits the post. What a 30 seconds of action. Where do you start? What a fantastic save by Mignon. He could well have just won his team this game. Harry Kane finds some space. It's a brilliant header. Nothing like late drama. Nothing like the Champions League to deliver it. For the first time in 11 years, one of the stellar names of European football are through to the last date of the Champions League. Tottenham's Antonio Conte era appears to be crumbling. It will be fascinating to see what the future holds. The future for Milan is a Champions League quarter-final. 0-0 on the night. Milan win. 1-0 on aggregate.