Inter Milan were knocked out of the Champions League after they could only manage a 1-1 draw at home to Group B's bottom club PSV Eindhoven on Tuesday to finish third behind Tottenham Hotspur.
Inter would have qualified with a win but, on a fraught night at San Siro, finished level on eight points with Tottenham who squeezed through after drawing 1-1 away to Barcelona due to their better head-to-head record over the Italians.
PSV, with only one point from their first five games, took a shock lead in the 13th minute when Hirving Lozano headed home after Kwadwo Asamoah lost possession in defence.
In a match which Inter coach Luciano Spalletti described as the most important of his 18 months at the club, the visitors then survived incessant Inter pressure until Mauro Icardi headed in from Matteo Politano's cross in the 73rd minute.
Inter were twice close to snatching a win in stoppage time, first when Icardi had the ball taken off his toe by a brilliant last-ditch tackle and then when substitute Lautaro Martinez headed over Ivan Perisic's cross from an unmarked position.
Despite their dominance, Inter were often nervous and careless and looked strangely subdued immediately after Tottenham's late equaliser was announced in the stadium.
"We didn't keep the necessary tranquility, we got too nervous and we lost too many balls which created disorder on a tactical level," said Spalletti.
"If you get too tense, you lose the vision of the match. We need the right mental strength to react to events such as the result of the Barcelona game... We got carried away by the tension."
Inter made a whirlwind start and, after Perisic saw his header pushed onto the post by Jeroen Zoet, got a huge boost when Barca took an early lead in the other game.
But the celebrations were short-lived as minutes later Asamoah tried to turn past Steven Bergwijn and was dispossessed by the Eindhoven forward, who crossed to the far post where Lozano headed in.
The Ghanaian's nightmare continued when he slid to break up an Eindhoven attack but succeeded only in setting up an opening for Luuk de Jong whose shot was blocked by Inter keeper Samir Handanovic.
Icardi headed wide from a Perisic cross and again from the tricky Matteo Politano as Inter flung a series of balls into the Eindhoven area without success.
Inter continued to press desperately after the break, and Icardi had a shot brilliantly turned around the post by Zoet, who then blocked a low effort from Politano.
They eventually leveled when Politano floated a long cross to the far post, where Icardi got free of Trent Sainsbury to squeeze his header past Zoet.
At that point, Inter were heading through to the next round. But their dreams were crushed late in the game when Tottenham equalised in Barcelona, silencing San Siro.
"I enjoyed the way we fought all the way tonight," said PSV coach Mark van Bommel. "We played with courage and imagination, and not just here.
"We took the lead in four of the six games. We should have got more out of them. We have shown that we can go toe-to-toe with top European teams."