Match ends, Inter Milan 2, Tottenham Hotspur 1.
Late goals from Mauro Icardi and Matias Vecino stunned Tottenham as Inter Milan celebrated their return to the Champions League with a dramatic Group B win.
Christian Eriksen's deflected strike earlier in the second half looked to have been decisive for Spurs, who stepped up a gear after an unconvincing first period, beset by poor passing.
However, Argentine Icardi, a peripheral figure for long periods, levelled with a 20-yard volley five minutes from time.
And Uruguayan midfielder Vecino then headed a winner in added time to send Spurs to a third consecutive defeat.
It had looked like being a good evening for Mauricio Pochettino's side, even if they started as though back-to-back Premier League defeats by Watford and Liverpool had taken their toll.
If that encouraged a vociferous San Siro crowd, Luciano Spalleti's team were unable to capitalise.
Instead they carried their indifferent Serie A form - they are 15th after winning just one of their first four games - into European competition, and were eventually punished by Denmark midfielder Eriksen.
The 26-year-old was the visitors' stand-out performer and followed up on his own parried shot to give Spurs the lead with an effort that veered over goalkeeper Samir Handanovic via a nick off Inter defender Miranda.
For drama, it all looked a far cry from the clubs' last meeting in the competition in 2010, when the Italians led 4-0 after 35 minutes before a 21-year-old Gareth Bale announced himself with a hat-trick that nearly transformed the game.
But drama there was, at the very last, as Inter first looked to have salvaged a point, and then stole all three to follow group leaders Barcelona with a opening-day win.
Contrasting fortunes for Kane & Icardi
It was a night of contrasting fortunes for Harry Kane and his opposite number Icardi, who both average better than a goal every two games for their clubs.
They shared the frustration of being isolated for long periods, with Icardi touching the ball 15 times and Kane 25.
While Kane did some of his best work in central positions linking the play with team-mates, it was his failure to convert a glorious first-half opportunity that will again raise question marks over his form and fitness.
Having rounded goalkeeper Handanovic, Kane, the World Cup Golden Boot winner, ran the ball out of play with the goal at his mercy.
In contrast, the Argentina forward inspired a remarkable turnaround with his first effort on goal - dispatching Kwadwo Asamoah's left-wing cross with a sumptuous volley that flew into the bottom left corner.
Change in personnel, familiar problem for Spurs
With his side beginning their third successive Champions League campaign, Pochettino deployed eight of the players who ran Juventus close in their last-16 tie last season.
However, Toby Alderweireld and Kieran Trippier were both omitted by the Spurs manager, after featuring in the defeat by Liverpool.
Yet despite the change of personnel, it was the same flaw - defending set-pieces - that has hamstrung Tottenham in three consecutive 2-1 defeats in evidence again when Vecino scored late on.
"They were on the pitch against Liverpool and Watford," Pochettino said of the omitted pair, who were not with the squad.
"They are easy targets. We need to talk about football. You force me to say something that is not good. You disrespect the players who were here today. You can blame me on my selection of the starting XI but please don't disrespect the players on the pitch.
"Until 86 or 87 minutes, the game was under control. The problem is we didn't kill the game."
Tottenham's troubles in Italy - the stats
- Tottenham have won just one of their past 10 European matches away from home against Italian opposition (D4 L5).
- Inter Milan forward Mauro Icardi has scored in each of his past three appearances in European competition, after scoring just one in his previous 11 games.
- Inter Milan have won four of their past five Champions League matches against English teams (L1 - vs Spurs).
- Tottenham's Christian Eriksen has scored three goals in his past five Champions League appearances, one more than in his previous 24 in the competition.
- Harry Kane attempted no shots in this match for Tottenham - only the second time since the start of last season that Kane has not attempted a single shot in a match in which he has played at least 45 minutes for Spurs in all competitions (also vs Man City in April 2018).
- This is the first time that Spurs have lost three consecutive games in all competitions under Mauricio Pochettino and the first time since March 2014, under Tim Sherwood.
Tottenham visit Brighton in the Premier League on Saturday (kick-off 17:30 BST). Their next Champions League action sees them welcome Barcelona to Wembley on Wednesday, 3 October (20:00 BST). Inter travel to PSV Eindhoven the same night.
- 37SkriniarBooked at 21mins
- 6de Vrij
- 16PolitanoSubstituted forKeitaat 72'minutes
- 14NainggolanSubstituted forValeroat 89'minutes
- 44PerisicBooked at 43minsSubstituted forCandrevaat 64'minutes
- 13VormBooked at 82mins
- 6D SánchezBooked at 38mins
- 5VertonghenBooked at 51mins
- 11LamelaSubstituted forWinksat 72'minutes
- 7Son Heung-MinSubstituted forLucas Mouraat 64'minutes
- 10KaneSubstituted forRoseat 90'minutes
- 27Lucas Moura
- Clément Turpin
- Shots on Target
Second Half ends, Inter Milan 2, Tottenham Hotspur 1.
Goal! Inter Milan 2, Tottenham Hotspur 1. Matías Vecino (Inter Milan) header from very close range to the top left corner. Assisted by Stefan de Vrij with a headed pass following a corner.
Corner, Inter Milan. Conceded by Danny Rose.
Attempt blocked. Marcelo Brozovic (Inter Milan) left footed shot from outside the box is blocked.
Attempt blocked. Matías Vecino (Inter Milan) right footed shot from the centre of the box is blocked.
Attempt blocked. Matías Vecino (Inter Milan) left footed shot from the centre of the box is blocked. Assisted by Miranda.
Corner, Inter Milan. Conceded by Davinson Sánchez.
Substitution, Tottenham Hotspur. Danny Rose replaces Harry Kane.
Substitution, Inter Milan. Borja Valero replaces Radja Nainggolan.
Attempt missed. Lucas Moura (Tottenham Hotspur) right footed shot from the left side of the box is high and wide to the right. Assisted by Christian Eriksen.
Davinson Sánchez (Tottenham Hotspur) wins a free kick in the defensive half.
Foul by Mauro Icardi (Inter Milan).
Goal! Inter Milan 1, Tottenham Hotspur 1. Mauro Icardi (Inter Milan) right footed shot from outside the box to the bottom left corner. Assisted by Kwadwo Asamoah with a cross.
Attempt missed. Eric Dier (Tottenham Hotspur) right footed shot from outside the box is high and wide to the right.
Christian Eriksen (Tottenham Hotspur) wins a free kick on the right wing.
Foul by Miranda (Inter Milan).
Michel Vorm (Tottenham Hotspur) is shown the yellow card.
Attempt missed. Antonio Candreva (Inter Milan) right footed shot from the right side of the box is too high. Assisted by Radja Nainggolan.
Jan Vertonghen (Tottenham Hotspur) wins a free kick in the defensive half.