(CNN) -- Spain's Champions League woes continued as Sevilla were beaten 2-1 at home by CSKA Moscow to go out at the first knockout stage 3-2 on aggregate.
A disastrous goalkeeping error from their captain Andres Palop sealed Moscow's passage to the quarterfinals, the first time a Russian team has reached that stage in over a decade.
With the tie level at 2-2, Palop made a hash of a long-range free kick from Keisuke Honda as he could tried to punch the ball away and saw it fly into his net.
Sevilla pressed but could not find the two goals they then needed to avoid joining Spanish league leaders Real Madrid in exiting from Europe's premier club competition at the same stage.
It leaves just holders Barcelona, who are in action against VfB Stuttgart on Wednesday, as Spain's last hope in the competition.
Tomas Necid put CSKA ahead in the 39th minute lead only for Argentine Diego Perotti to equalize two minutes later and level the tie 2-2 on aggregate.
But Palop's error proved decisive.
"Of course it is a real shame to go out but we have to bounce back from this," home striker Alvaro Negredo told AFP.
"CSKA deserve it and you have to congratulate them even though it hurts."
Sevilla, who drew 1-1 in Moscow and looked favorites to go through, fielded a defensive line-up as coach Manolo Jimenez opted to leave the likes of Negredo and Mali star Frederic Kanoute on the bench.
Brazilian Luis Fabiano was left as a lone striker but it was winger Jesus Navas who missed a glorious chance to put them ahead after only three minutes but he shot straight at goalkeeper Igor Akinfeev.
The Russians, who are just back in action after their midwinter break, went ahead when Necid curled his shot home, but Navas then assisted as Perotti equalized almost immediately.
Sevilla had chances to move ahead before Palop's mistake which took the sting out of their challenge as CSKA reached the last eight of the Champions League for the first time.