Tottenham crashed out of the Champions League after failing to score against AC Milan in a miserable night in north London.
Spurs came into the second leg of their last-16 tie with a 1-0 deficit after defeat in Italy and failed to muster anything in front of goal. Antonio Conte returned to the touchline following his gall bladder surgery, but this result looked like it could spell the beginning of the end for his tenure in charge, with the Italian's contract expiring in the summer.
Spurs were booed off at half-time by a section of the home supporters following a dreadful first 45 minutes which contained no shots on target for either side. They improved after the break - they could hardly get worse - but a stubborn Milan defence ensured it took until the 64th minute for first shot on target from Pierre-Emile Hojbjerg.
Hojbjerg tried to rile the crowd, but that effort did not inspire a turnaround. Conte used his substitutes, but Spurs offered very little in front of goal until the third minute of injury time when Harry Kane forced Mike Maignan into a fine low save before Divock Origi hit the post at the other end.
To make matters worse, there was a red card for Cristian Romero for two idiotic challenges. Here are the talking points.
First half woes continue
Glenn Hoddle has a theory, and it's backed up by the statistics. Coming into this game eight of Tottenham's last 10 goals had been scored in front of the South Stand - the fantastic 17,500-seater wall of noise at their home stadium.
Tottenham tend to play towards the North Stand in the first half. And, quite often, very little happens. Spurs have a first-half goal scoring problem and it has never been more obvious than against AC Milan.
Spurs could have come racing out of the blocks, intent on reducing the 1-0 lead their visitors held from the first leg. But nothing of the sort emerged. Milan were extremely comfortable in the first half, with the Expected Goals tally telling a sad, sad story. It read: Tottenham 0.09, Milan 0.10. That was unacceptable for the home fans, who sent their side off to a volley of boos at the half-time whistle.
Conte agitated
While there was very little in the way of entertainment on the pitch, there was lots to look at on the sidelines, where Conte was in a constant fit of agitated movement. The Italian underwent surgery at the start of February to remove his gall bladder. Before this game he insisted he was fine and raring to go; now we know he was telling the truth.
He might have found his gall bladder surgery less painful than watching his dysfunctional side operate. At times they pressed in unison and forced Milan into surrendering possession, but they never did anything with it.
The five attacking starters of Kane, Song Heung-min, Dejan Kulusevski, Ivan Perisic and Emerson Royal looked completely out of sync with each other. The most Maignan had to do was bend down and scoop up a ball which was rolling harmlessly towards him.
Supporting cast not clicking
Son and Kulusevski were fantastic for Spurs last season. The South Korean claimed the Premier League's Golden Boot while the Swede made an immediate impact when he arrived from Juventus in January.
This season, though, both have been a shadow of their former selves. Kane is at his best when dropping deep to allow runners beyond him. The England captain has the hold-up play ability and passing range to unlock defences. But he did not have the chance to show off his skillset against Milan.
Kulusevski got a bit of room on the right-hand side, but continually overhit his crosses or made the wrong decision when he arrived at the penalty area. Son saw less of the ball and struggled to impose himself on the match.
Tomori leads Milan resistance
Fikayo Tomori has had something of a rollercoaster season with AC Milan. After impressing massively in the 2021/22 campaign, the Englishman has found things tougher going the second time around.
Given a start by Stefano Pioli, the former Chelsea defender put in an assured performance. His pace appeared to be the reason why he was given the nod, with his recovery runs bailing his side out early on.
There was six minutes on the clock when Kulusevski tried to burst beyond him with no luck. With England's Euro 2024 qualifiers on the horizon against Italy and Ukraine, Gareth Southgate might be taking notice.
Rash Romero
Could it get worse? Of course it could.
Romero has been at Spurs long enough to get a reputation for diving into challenges, picking fights and making rash decisions. This was textbook stuff from the Argentina international.
There were just 16 minutes on the clock when Romero jumped into a wild slide tackle and completely missed the ball. A yellow card was the obvious result, meaning Romero would be suspended for Spurs' next European game.
He could have been sent off earlier, but in the event he lasted to the 78th minute before launching into a lunge on Theo Hernandez by the touchline. The pitchside microphone picked up a howl from the AC Milan captain and Romero was given his marching orders.
