A quiet and sparsely-filled San Siro played host to a thrilling game of football that saw Spurs progress to the quarter finals of the Europa League by the skin of their teeth.
Inter Milan kicked the match off but a composed start from Tottenham saw them comfortably keeping Inter at bay, whilst also playing some neat passing moves themselves.
However, it was Inter who opened the scoring after 20 minutes. A slick counter-attacking move from the Italians resulted in a totally free Antonio Cassano getting his head to a cross from Rodrigo Palacio, nodding downwards to beat Brad Friedel at his right hand post.
Five minutes later, Cassano returned the favour and played Palacio through on goal. The Argentinian had Friedel beaten again, but his lobbed effort hit the crossbar and bounced over.
The rest of the first half was very tentative from both teams, as neither wanted to concede any more goals, with the best chances falling to Spurs – Kyle Walker directing a header from a crossed Gylfi Sigurdsson free kick just wide after 36 minutes and Adebeyor chipping just over in injury time – and the half ended with Inter a single goal up.
Spurs got the second half underway and both teams looked very nervous early on, making some sloppy mistakes.
The first real chance of the second half came when Jan Vertonghen found Adebayor and the Togolese forward made a great run and squared back to Vertonghen, who was charging forward but, despite the Belgian’s rampant goalscoring form of late, he miscued.
They would be made to pay for that miss, as Rodrigo Palacio was put through on goal and calmly finished to put Inter two up just a minute later on 52 minutes.
This caused Spurs to shift formation on 56 minutes, with Lewis Holtby being brought on for Jermain Defoe as Spurs opted to compete more in midfield.
A very quiet spell ensued, with very little happening until both teams made a substitution, with Spurs bringing on Aaron Lennon and Inter bringing on Ricardo Alvarez within a couple of minutes around the 70 minute mark.
After 75 minutes, Inter drew the tie level as Antonio Cassano fired in a free kick. He shot, it hit the wall, then deflected off William Gallas, who will be credited with the own goal, in to the Tottenham net.
Neither team did anything for the next 15 minutes, until Esteban Cambiasso was through on goal in injury time, but the Argentine dragged his shot inches wide and the match went to extra time, tied at 3-3 on aggregate.
Inter immediately went after a winning goal, showing more initial intent, but it was Spurs who had the first chance 2 minutes in when Lennon was put through on goal. Zanetti blocked, however, and the ball went out a corner.
The resulting corner was met by the head of Vertonghen and only an excellent Handanovic save prevented a key away goal. Another corner followed and William Gallas headed wide when he was totally unchallenged.
Spurs then got that all-important away goal, when Moussa Dembele struck a 20 yard shot that Handanovic could only parry and Adebayor followed up to tap in the rebound. This left Inter needing two goals. It also meant that Adebayor has now scored for Spurs against Inter and for Arsenal against AC Milan in the San Siro.
Very little in terms of chances occurred until the final minute of the first half of extra time, when Palacio headed straight at Friedel. In doing so, he injured Moussa Dembele, elbowing him in the head. The Belgian had to be taken off, leaving Spurs temporarily with ten men, having used all of their substitutes – he did however return to the game, but not before Inter took advantage and threatened the Tottenham goal a couple of times.
Half time of extra time ended with Inter leading 3-1 on the night, but losing 4-3 on aggregate and needing two goals to progress.
Brad Friedel made a fantastic stretching save from Cassano’s long-distance effort just thirty seconds in to the second half, tipping the ball out for a corner.
Inter scored a fourth after 110 minutes, when Cassano crossed for Alvarez to head home past a flailing Brad Friedel.
Handanovic came up for a corner in the 119th minute which Andrea Ranocchia ultimately got his head to, but he put it well over.
Spurs had to face two minutes of stoppage time after the initial 120 as they defended desperately, but the referee mercifully brought the match to a close and Spurs went through on away goals.
Referee: Ivan Bebek.
Handanovic; Jonathan (Ranocchia, 107), Juan Jesus, Chivu, Zanetti; Gargano, Kovacic (Benassi, 79), Cambiasso, Guarin (Alvarez, 71); Cassano, Palacio.
Friedel; Walker, Gallas, Vertonghen, Naughton (Caulker, 103); Dembele, Livermore (Lennon, 70), Parker, Sigurdsson; Adebayor, Defoe (Holtby, 56).
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