Sheffield Wednesday scored twice in three minutes as they came from behind to earn a draw on manager Alan Irvine's return to Preston North End.
Billy Jones saw a shot blocked by Darren Purse but Neil Mellor reacted quickly to put North End ahead with a low right-foot strike.
Lee Grant denied Mellor before Paul Coutts scored with a low strike.
But Andy Lonergan failed to stop Tommy Miller's 30-yard strike and Marcus Tudgay equalised with a lofted finish.
It was Irvine's first visit to Deepdale since he was sacked as Preston manager in December.
And his struggling team might have collected all three points but Lonergan made two excellent late saves to deny Leon Clarke.
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Chelsea 0 - 1 Inter Milan (agg 1 - 3)
Jose Mourinho returned to Stamford Bridge in triumph as Inter Milan sent Chelsea crashing out of the Champions League.
Samuel Eto's clinical strike 11 minutes from time settled a scrappy encounter and sealed a place in the quarter-finals for Mourinho at the expense of the club he left in 2007 after a hugely successful three-and-a-half years.
And the misery for Chelsea and coach Carlo Ancelotti was complete when Didier Drogba was sent off in the closing minutes after a penalty area clash with Thiago Motta.
Mourinho's Inter were able to keep a subdued Chelsea at arm's length for the majority of a tense evening littered with fouls and spells of ill-feeling, with even the self-appointed "Special One" being targeted for abuse by the supporters who once idolised him as frustration spread around Stamford Bridge in the closing moments.
He celebrated in relatively muted fashion when Eto'o capped a spell of Inter pressure with the crucial goal, after Diego Milito had missed the chance to seal Chelsea's fate even earlier.
Chelsea had their moments in a frantic first half, with Michael Ballack shooting just wide and Nicolas Anelka seeing a close-range effort cleared off the line by Motta, while keeper Julio Cesar saved well from Florent Malouda after the break.
And Chelsea were also left claiming they were victims of a clear injustice in the first half when Drogba was dragged to the ground by Walter Samuel as they wrestled to reach a corner.
This apart, Inter were able to restrict Chelsea, who failed to show the wit and guile required to break them down, demonstrating the defensive discipline and resilience that is the trademark of any Mourinho team.
He did not milk Inter's win at the final whistle, but Mourinho may just appreciate the irony of the fact that he has ended Chelsea owner Roman Abramovich's dream of bringing the Champions League to Stamford Bridge.
For Ancelotti and Chelsea, the task is now to regroup and refocus their sights on the Premier League and the FA Cup.
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After another disappointing season where Roma finished one place below tonight’s hosts, “Giallorossi” come into new one with almost the same players. Club didn’t reach Champions League which caused a limited resources for new signings. Only worth of mentioning are Nicolas Burdisso who came on loan from Internazionale and winger Stefano Guberti (ex Ascoli). They even sold excellent Alberto Aquilani to Liverpool to balance the books. Fans expected one new striker, but so far no big news about that. The main target this season will be the spot for Champions League, but the capabilities of this team are under the question mark. They force attacking style of play, all their friendlies and European encounters (against Gent and Kosice) were high scoring games. Prince of Roma, Francesco Totti plays in great shape, despite the years, while young French Jérémy Menez finally started to repay 10 mill. that have been spent on him last year. There’re also two more excellent attackers, Mirko Vucinic and Júlio Baptista. But, as Genoa, Roma lack in defence line which will be even weaker tonight for Philippe Mexès and first goalkeeper Doni. Also, Luciano Spalletti can not count on Vucinic and Perotta. Defeat in the first round is unacceptable and visitors will go for all three points.