Tottenham’s season plunged to new depths after they were dumped out of the Champions League following a 1-0 aggregate defeat to AC Milan.
In a week that saw them knocked out of the FA Cup to Championship side Sheffield United and then lose ground in the Premier League top-four race with defeat to relegation-threatened Wolves, Spurs were unable to overturn their first-leg deficit after a limp 0-0 second-leg draw at the Tottenham Hotspur Stadium.
Their exit heaped further doubt over boss Antonio Conte’s future and the Italian’s likely exit might well be expedited after the atmosphere turned toxic with the fans angrily voicing their disapproval at full-time.
This was as bad a performance as Spurs could have put in and never looked like turning the tie around, managing just two efforts on target. Cristian Romero only made matters worse with the unprofessional way he was sent off in the final 15 minutes.
Heavy traffic around the north London area led to a 10-minute delay to kick-off, with both teams arriving to the stadium late.
It helped build the atmosphere, but Spurs did not respond with a strong start as Milan were composed in possession and pressed the hosts well.
And it was the visitors who had the chance to extend their lead as they opened Spurs up with a well-worked free-kick in the 19th minute.
In wet conditions and with a whistle-happy referee, it was a damaging opening 21 minutes as Romero and Clement Lenglet were both booked, which would have ruled them out of the next match. But that proved inconsequential.
Tottenham’s performance was not out of the ordinary for this season – they have regularly been lethargic in first halves – but they lacked the urgency and spark that was befitting of a game of this stake.
The second half promised to be a different affair, but it was again the Italian side that forged a real opening.
An injury to Ivan Perisic saw the introduction of Pedro Porro and that finally altered the complexion of the game as the Spaniard showed the attacking intent that had been otherwise absent.
That finally translated into a goal threat and Spurs’ first meaningful effort came in the 64th minute when Pierre-Emile Hojbjerg worked his way into the box and tested Milan goalkeeper Mike Maignan with a fierce effort which was tipped over the bar.
The game was being played in Milan’s half, but that made the visitors a threat on the break and they had two good chances.
Spurs were getting more and more frustrated and their task got even harder when Romero was shown a second yellow card for a reckless foul on Theo Hernandez.
Milan could easily have gone on to win by a more convincing margin had they showed more composure with Diaz and Ismael Bennacer being denied by Forster.
Harry Kane, who will surely be thinking about his future now more than ever, almost sent it into extra-time but his powerful header was well saved by Maignan before Divock Origi hit the post at the death.