UEFA Cup action ends in penalty shootout defeats for both Tottenham and Everton.
England's night of UEFA Cup action ended in penalty shootout defeats for both Tottenham and Everton while Marseille's elimination ended France's participation in European club action this season.
Competition favourites Bayern sailed through at the expense of Belgian club Anderlecht but English hopes must now bank on Bolton winning at Sporting Lisbon on Thursday to have a presence in the quarter-finals.
Tottenham came back from a 1-0 first leg deficit to level the tie at 1-1 against PSV Eindhoven thanks to Dimitar Berbatov, bringing about extra time, but it was the Dutchmen who held on to win 6-5 in the shootout.
Aiyegbeni Yakubu's spot-kick against the post condemned Everton to their exit after they lost 4-2 in a penalty shoot-out to Fiorentina at Goodison Park.
The English Premiership team had taken this last sixteen second-leg into extra-time after goals from Andy Johnson and Mikel Arteta cancelled out the Italian club's 2-0 first-leg lead.
But misses by Yakubu and Phil Jagielka in the shoot-out enabled Fiorentina to book their place in the last eight -- despite being outplayed by Everton throughout the game.
Having been lucky to escape with just a 2-0 defeat from the first-leg in Florence last Thursday, Everton were fully aware of the task that they faced against Cesare Prandelli's Serie A high-flyers.
Two goals from Zenit St Petersburg's Pavel Pogrebnyak earned the Russian side a 2-0 victory over Marseille to book their quarter-final berth on Wednesday.
Marseille's conceded away goal in the 3-1 first leg victory in France proved the deciding factor as they went out of Europe's second-tier club competition on away goals after a 3-3 aggregate scoreline.
"I was really impressed by my players who showed a great quality of play on a difficult pitch," said Zenit's Dutch coach Dick Advocaat. "The away goal was the good news of this tie."
Andrei Arshavin started the move for the first goal in the 38th minute. He passed the ball to Konstantin Zyrianov who set up Pogrebnyak to beat the offside trap and the striker shot past Marseille keeper Steve Mandanda.
Cisse could have got an equaliser four minutes later but the former top scorer in the French league, set on his way by Valbuena, fired straight at keeper Viacheslav Malafeev.
Zenit, who had the better of Marseille in the ballwinning stakes, could have made the most of a poor spell by Gerets' side just after the break but later in the half Marseille lifted themselves and Niang had a shot which just missed the Russians' goal.
The second and decisive goal came in the 77th minute when Fatih Tekke got a touch to feed Pogrebnyak for his second strike, and, despite a late flurry from Niang and Cisse, it was the home crowd which celebrated victory.
The defeat was even more bitter for the French as Marseille defender Ronald Zubar complained of racist chants by some Russian fans directed against him and black teammates Charles Kabore and Andre Ayew.
"They threw a banana at us and made monkey sounds," complained the player from the French Caribbean island of Guadeloupe.
"It's not great. That makes the defeat worse, while they had everything to celebrate. We would have preferred that the match was stopped and the individuals removed."