Chelsea lost 3-2 to Rubin Kazan on the night but went through to the Europa League semi-finals 5-4 on aggregate after a topsy-turvy match in Russia.
Playing at the Luzhniki stadium in Moscow, the hosts trailed twice as they chased a 3-1 deficit from the first leg, but despite a spirited late effort they were unable to put three goals between them and the Blues.
Fernando Torres, who scored twice in the first leg in London, opened the scoring with a fifth-minute lob. Rubin levelled through Ivan Marcano’s power header, but Victor Moses dampened their hopes soon afterwards to get Chelsea a second away goal.
With neither side particularly interested in defending, the hosts equalised a second time as Gokdeniz Karadeniz exploited slack marking to head home, and they went ahead for the first time as Natcho converted a penalty.
Salomon Rondon spurned a late opportunity to give Chelsea the jitters, but the Russians could not add to their lead. They had needed two more goals anyway, meaning it was ultimately a relatively comfortable passage for Rafael Benitez's side.
The result means Chelsea could become the first team to win Europe’s secondary club competition the season following a Champions League victory.
All three of Rubin’s goals came from unconscionable individual errors, although it was far from a first-choice back four as John Terry, Paulo Ferreira and Cesar Azpilicueta joined David Luiz in defence.
Chelsea held a commanding lead from the first leg but needed to ensure they kept things tight early on, as the away goal at Stamford Bridge meant a 2-0 Rubin win would have sufficed.
Initially the hosts looked lively but Chelsea were sitting back and, at the first time of asking, they nabbed a tie-killing goal.
It was a route one move as Lampard swung a long ball into the space ahead of Torres – he had got the better of the Rubin defence but there was no reason for keeper Sergei Ryzhikov to come rushing out of his box, allowing the Spaniard to lob from 30 yards into an empty net.
The advantage was now insurmountable and Rubin seemed broken by it, retreating into their shell for a forgettable half hour that saw Chelsea barely bother with the counter attack.
Rubin did snap out of their malaise at the end of the first half, Gokdeniz Karadeniz forcing a smart stop from Petr Cech after beating John Terry to Natcho’s pass, and they continued the momentum into the second period.
John Terry has been relegated to bit-part player in recent months and it is easy to see why at times. His inability to complete a routine defensive header, followed by a bungled attempt to clear his lines, saw the Blues skipper concede a needless corner, from which Spanish defender Marcano headed home for 1-1.
Rubin had a faint glimmer of hope but it was soon extinguished by Moses who, after a fine Lampard through ball, completed a cool one-two with Ramires before firing home.
That meant the hosts needed to score four more goals to go through, and they gave it their best shot.
Within six minutes they were level again as Turkey midfielder Gokdeniz – who is 5’6” tall – managed to beat 6’2” Luiz to a header, which he placed low past Cech for 2-2.
Marcano then headed inches wide and a third goal seemed inevitable, although this too came from horrible defending as Azpilicueta gave away a needless penalty with a foul on substitute Aleksandr Ryazantsev.
Natcho – who had been the best player on the park – hammered the spot-kick into the roof of the net, meaning Rubin needed two goals in around 20 minutes to dump Chelsea out.
They had a proper go at it too, although only managed to create one clear-cut chance as Rondon somehow headed straight at Cech from six yards.
Chelsea, meanwhile, could have had a few on the counter as Moses and Oscar spurned decent chances, and in the latter stages they had the ball and match under control as they played out the final seconds.
MAN OF THE MATCH
Gokdeniz Karadeniz (Rubin) – The Turkish playmaker was a constant threat, scoring one goal and denied another by Petr Cech.
RUBIN: Ryzhikov 5, Kuzmin 5, Ansaldi 7, Navas 6, Marcano 7, Orbaiz 5, Kasaev 6, Eremenko 6, Karadeniz 8, Natcho 8, Rondon 5. Substitutes: Kaleshin 6, Ryazantsev 7, Dyadyun 7
CHELSEA: Cech 7; Azpilicueta 5, Luiz 5, Terry 5, Ferreira 6; Ake 6, Lampard 7; Ramires 7, Benayoun 6, Moses 7; Torres 7. Substitutes: Oscar 5, Mikel 6, Ivanovic N/A
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