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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.
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.
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 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.
