Everton, Tottenham and Bolton failed to match the lofty heights of their Champions League counterparts on Thursday as their UEFA Cup dreams were left hanging in the balance.
Hopes were high that the three could follow the impressive examples set by Manchester United, Chelsea and Arsenal midweek, but all three endured disappointing nights.
Everton, who harbor hopes of playing in Europe's elite competition next season, slumped to a 2-0 defeat at Fiorentina in their last 16, first leg clash to lose their 100 percent record in the competition.
PHOTO: AP
Tottenham were also beaten, going down 1-0 at White Hart Lane to PSV Eindhoven to shatter coach Juande Ramos' hopes of winning the competition for the third successive year.
Bolton, battling relegation from the Premier League, drew 1-1 at home to Sporting Lisbon.
Glasgow Rangers kept British pride intact with a 2-0 win at home to Werder Bremen, while title favorites Bayern Munich cruised to a 5-0 win at Anderlecht.
PHOTO: AP
Everton were indebted to goalkeeper Tim Howard who celebrated his 29th birthday in style with a string of fine first-half saves in the cold and rainswept Artemio Franchi Stadium in Florence.
But Fiorentina were deserving winners with second half goals from Serbian striker Zdravko Kuzmanovic and midfielder Ricardo Montolivo.
"We were a little too negative and too cautious," Everton skipper Phil Neville said. "We didn't play the way we could so it was a let down. We'll have to play at a higher tempo in the second leg next Wednesday, put in crosses and create chances."
Tottenham Hotspur's English League Cup final hangover showed no sign of abating as PSV Eindhoven took a 1-0 advantage back to the Netherlands.
Jefferson Farfan punished a horrendous first half mistake from debutant Gilberto to inflict a second successive defeat on Juande Ramos' side since they won the League Cup two weeks ago.
At the Reebok, Bolton Wanderers saw Sporting Lisbon's Simon Vukcevic crack a stunning equalizer to cancel out Gavin McCann's first-half opener and leave Gary Megson's side facing an uphill struggle in Portugal.
Celtic may have been eliminated from the Champions League by Barcelona but city rivals Rangers stayed on course in the UEFA Cup with a 2-0 win over Werder Bremen thanks to goals either side of halftime from Gabon international Daniel Cousin and Northern Ireland midfielder Steven Davis.
"Early on Bremen had a lot of possession, but scoring just before halftime was a big factor for us and then scoring at the start of the second half put us in a great position," Rangers boss Walter Smith said.
"But it was also vital we didn't concede a goal at home and that could be important in the second leg," he said.
Former European champions Bayern Munich were the night's most impressive winners, clinching victory against Anderlecht in Brussels for the first time in five meetings.
Hamit Altintop, Luca Toni, Lukas Podolski, Miroslav Klose and Frank Ribery were all on target, while Anderlecht were also reduced to 10 men after the sending off of Polish defender Marcin Wasilewski right on the stroke of halftime.
Marseille, also former European champions, moved closer to the last eight with a 3-1 win over Russia's Zenit St. Petersburg with former Liverpool striker Djibril Cisse scoring twice.
Bologna on Thursday advanced past Empoli to reach their first Coppa Italia final in more than half a century. Thijs Dallinga’s 87th-minute header earned Bologna a 2-1 win and his side advanced 5-1 on aggregate. Giovanni Fabbian opened the scoring for Bologna with a header seven minutes in. Then Viktor Kovalenko equalized for Empoli in the 30th minute by turning in a rebound to finish off a counterattack. Bologna won the first leg 3-0. In the May 14 final in Rome, Bologna are to face AC Milan, who eliminated city rivals Inter 4-1 on aggregate following a 3-0 win on Wednesday. Bologna last reached the
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