Tottenham Hotspur's Champions League campaign ended in bitterly disappointing fashion as they failed to overturn a first-leg deficit in the last 16 against AC Milan.
Spurs paid the price for another passive start that allowed Milan to settle into their task - the misery complete when defender Cristian Romero was sent off late on after receiving a second yellow card for a wild challenge on Theo Hernandez.
Pierre-Emile Hojbjerg tested AC Milan keeper Mike Maignan with a powerful second-half shot and Harry Kane headed wide, but Spurs failed to mount sustained pressure on the Italian defence.
A late Kane header was brilliantly kept out by Maignan before Divock Origi struck the post for the visitors as Spurs went out tamely, their season now resting on the battle for a top-four place in the Premier League.
Spurs simply not good enough
Spurs fans reacted angrily as their Champions League campaign came to a conclusion and their discontent was understandable after such a dismal performance.
The lack of urgency that has marked so much of their season has never been more stark than in the first 45 minutes when Spurs played as if they were barely aware they needed to score to keep their ambitions alive.
Manager Antonio Conte returned to the technical area after recuperating from gallbladder surgery but this did not spare him the wrath of the Spurs support mystified by such a conservative approach.
He was not helped by Romero's red card for a late, reckless tackle on Hernandez, having already received a first-half caution for a clumsy challenge to prevent Rafael Leao breaking clear.
Kane almost rescued Spurs and sent the game into extra time with that late header, but for most of the night he was starved of meaningful service in a side largely devoid of creativity.
What this means for Conte's long-term future remains to be seen, with growing uncertainty surrounding his position and his contract up at the end of the season.
Spurs now have only that top-four place to fight for, and on this form you would not back them to achieve it. They have scrambled through much of this season despite indifferent form but there was to be no reprieve here - and they did not deserve one.
Tomori top class for Milan
Fikayo Tomori has slipped out of the England reckoning, but his calm and measured performance was a timely reminder of the qualities he can offer should manager Gareth Southgate require them.
The 25-year-old former Chelsea defender has matured in Serie A and was a rock in the Milan defence here - strong in the air, showing impeccable timing with his tackles and calm on the ground.
Spurs hardly subjected Milan to intense scrutiny, but when needed Tomori was excellent and a key figure as they reached the quarter-finals.
Milan were also well-served by keeper Maignan, faultless throughout and producing a moment of brilliance to keep out Kane in the closing seconds.
Spurs can have no complaints over the two legs, with Milan probably surprised by the absence of intensity in front of a home crowd waiting for the opportunity to roar their side on.
Player of the match
BennacerIsmaël Bennacer
AC Milan
Squad number4Player nameBennacer
Squad number9Player nameGiroud
Squad number27Player nameOrigi
Squad number19Player nameHernández
Squad number23Player nameTomori
Squad number17Player nameRafael Leão
Squad number10Player nameDíaz
Squad number8Player nameTonali
Squad number56Player nameSaelemaekers
Squad number16Player nameMaignan
Squad number28Player nameThiaw
Squad number12Player nameRebic
Squad number20Player nameKalulu
Squad number30Player nameJunior Messias
Squad number33Player nameKrunic
Line-ups
Tottenham
Formation 3-4-2-1
20Forster
17Romero34Lenglet33Davies
12Emerson Royal4Skipp5Højbjerg14Perisic
21Kulusevski7Son Heung-min
10Kane
20Forster17RomeroBooked at 78mins34LengletBooked at 21mins33Davies12Emerson RoyalSubstituted forRicharlisonat 70'minutes4SkippBooked at 90mins5Højbjerg14PerisicSubstituted forPorroat 53'minutes21KulusevskiSubstituted forD Sánchezat 83'minutes7Son Heung-min10KaneSubstitutes
6D Sánchez9Richarlison16Danjuma23Porro25Tanganga27Lucas Moura29Sarr40Austin41Whiteman45DevineAC Milan
Formation 3-4-2-1
16Maignan
20Kalulu28Thiaw23Tomori
30Messias33Krunic8Tonali19Hernández
10Díaz17Rafael Leão
9Giroud
16Maignan20Kalulu28ThiawBooked at 90mins23Tomori30MessiasSubstituted forSaelemaekersat 56'minutes33Krunic8Tonali19Hernández10DíazSubstituted forBennacerat 81'minutes17Rafael LeãoSubstituted forRebicat 89'minutes9GiroudSubstituted forOrigiat 81'minutesSubstitutes
2Calabria4Bennacer5Ballo-Touré12Rebic24Kjaer25Florenzi27Origi32Pobega46Gabbia56Saelemaekers83Mirante90De KetelaereReferee:Clément TurpinAttendance:61,602Live Text
Match ends, Tottenham Hotspur 0, AC Milan 0.
Second Half ends, Tottenham Hotspur 0, AC Milan 0.
Oliver Skipp (Tottenham Hotspur) is shown the yellow card for a bad foul.
Foul by Oliver Skipp (Tottenham Hotspur).
Sandro Tonali (AC Milan) wins a free kick in the defensive half.
Richarlison (Tottenham Hotspur) wins a free kick on the right wing.
Foul by Malick Thiaw (AC Milan).
Divock Origi (AC Milan) hits the right post with a left footed shot from the centre of the box. Assisted by Theo Hernández following a fast break.
Attempt saved. Harry Kane (Tottenham Hotspur) header from the centre of the box is saved in the bottom left corner. Assisted by Son Heung-Min.
Malick Thiaw (AC Milan) is shown the yellow card for a bad foul.
Pierre-Emile Højbjerg (Tottenham Hotspur) wins a free kick in the attacking half.
Foul by Malick Thiaw (AC Milan).
Foul by Pedro Porro (Tottenham Hotspur).
Ante Rebic (AC Milan) wins a free kick on the left wing.
Attempt blocked. Divock Origi (AC Milan) right footed shot from outside the box is blocked. Assisted by Alexis Saelemaekers.
Substitution, AC Milan. Ante Rebic replaces Rafael Leão.
Foul by Ben Davies (Tottenham Hotspur).
Rafael Leão (AC Milan) wins a free kick in the attacking half.
Attempt saved. Ismaël Bennacer (AC Milan) left footed shot from outside the box is saved in the bottom right corner. Assisted by Pierre Kalulu.
Attempt blocked. Sandro Tonali (AC Milan) right footed shot from the centre of the box is blocked. Assisted by Rafael Leão.