Inter beat Tottenham 4-1 in extra time for an extraordinary comeback, but heartbreakingly go out on away goals, 4-4 on aggregate.
The Nerazzurri lost 3-0 at White Hart Lane and their crisis continued at the weekend with a home defeat to Bologna, so there were seemingly few hopes for them. The absentee list included Diego Milito, Walter Samuel, Yuto Nagatomo, Matias Silvestre, Gaby Mudingayi, Joel Obi, Tommaso Rocchi, Zdravko Kuzmanovic and Ezequiel Schelotto, plus the suspended Alvaro Pereira. Gareth Bale was suspended for Spurs, but Emmanuel Adebayor stepped in.
Antonio Cassano fired straight at Brad Friedel on the counter-attack, while Jake Livermore was booked for time-wasting after just 14 minutes.
Cassano ran into the box again and went down too easily under William Gallas, so penalty appeals were waved away.
Inter broke through after 20 minutes with a splendid move. Jonathan rolled forward for Rodrigo Palacio down the right and his cross found Cassano unmarked at the back post for a header into the ground from six yards.
Gylfi Sigurdsson hit back with a curler that Samir Handanovic palmed away, but it was so nearly 2-0 when Cassano allowed Palacio to spring the offside trap and his chip cracked against the crossbar of an open goal.
Friedel looked anxious and had to rush off his line to clear from Palacio and Kyle Walker nodded wide from a Sigurdsson free kick. Before the break, Palacio put another ball across the face of goal, but this time too long to reach Esteban Cambiasso.
Fredy Guarin sprung the offside trap and stepped inside to smash a powerful angled drive that stung Friedel’s palms.
Adebayor had the chance to get Tottenham’s away goal in first half stoppages when Juan Jesus lost the ball, but Handanovic was quick off his line and did enough to put him off as the lob sailed over the bar.
Palacio dribbled into the area and was cut off by William Gallas, but 30 seconds later La Trenza got through to score.
He timed his run on to a Cambiasso through ball to get round Gallas and kept his cool to side-foot into the far bottom corner.
Inter were now back in the tie with 3-2 on aggregate and needed just one more to level it, though an away goal for Spurs would be disastrous.
The age-less Javier Zanetti skipped past Lewis Holtby and tested Friedel at the near post. The incredible comeback from 3-0 down to 3-3 on aggregate was completed when Cassano’s free kick was deflected and Gallas sliced it into his own net!
Palacio chested down a cross-field pass and Aaron Lennon was quick to intercept before he could pull the trigger from six yards.
Handanovic needed a great flying save to palm Kyle Naughton’s long-range screamer just round the base of the post.
There was a bizarre moment when Cassano collided with the referee and both were badly winded. Friedel had to smother a deflected Ricky Alvarez effort, then Palacio fired over after a mazy run past two Spurs players.
At the 92nd minute Cassano’s fancy footwork and a Tottenham slip let Cambiasso clear on goal, but his angled drive scraped the base of the far post, inches wide of an Inter victory.
Into extra time, Zanetti crucially blocked Lennon and from the corner Handanovic pushed Jan Vertonghen’s header off the line. From another corner, Gallas turned his free header off target.
It was a warning and Spurs got their away goal when Handanovic at full stretch parried a Moussa Dembele angled drive into the path of Adebayor to tap in the rebound.
Now it was not only 4-3 on aggregate to Tottenham, but Inter needed two goals to qualify for the quarter-finals.
Friedel smothered a Palacio header, but he clashed with Dembele during the move and the Tottenham man needed treatment.
Palacio tested Friedel again with a strike from a tight angle towards the near stick, while the goalkeeper flew to palm away a Cassano curler.
Andrea Ranocchia came on for the second half of extra time, wearing a protective mask after undergoing surgery for a fractured nose on Monday. The defender went to play as a centre-forward, a role he also adopted during the closing stages of the 1-0 defeat to Bologna.
Inter kept the tie alive yet again as Cassano curled a great cross to the six-yard box where an unmarked Alvarez nodded in past a flailing Friedel.
It was now 4-4 on aggregate, but Inter needed one more to win due to the away goals rule.
Ranocchia nodded a corner wide and Handanovic came up for a corner at the 119th minute, but Ranocchia again got the header over.
Ultimately the amazing comeback was not enough and Inter went out of the Europa League on away goals, 4-4 on aggregate, but showed pride, grit and made up for the awful first leg performance.
Inter 4-1 Tottenham aet (4-4 on agg)
Scorers: Cassano 20 (I), Palacio 52 (I), Gallas og 75 (I), Adebayor 96 (T), Alvarez 110 (I)
Inter: Handanovic; Jonathan (Ranocchia 107), Juan Jesus, Chivu, Zanetti; Gargano, Kovacic (Benassi 78), Cambiasso; Guarin (Alvarez 71); Palacio, Cassano
Tottenham: Friedel; Walker, Gallas, Vertonghen, Naughton (Caulker 104); Dembele, Parker, Livermore (Lennon 70), Sigurdsson; Defoe (Holtby 56), Adebayor
Ref: Bebek (CRO)