Everton, Tottenham and Bolton failed to match the lofty heights of their UEFA 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 in midweek, but all three endured disappointing nights.
Everton, who harbour 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 suffer their first loss since January and lose their 100-percent record in the competition.
Tottenham were also beaten, going down 1-0 at White Hart Lane to PSV Eindhoven to shatter coach Juande Ramos's 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 favourites Bayern Munich cruised to a 5-0 win at Anderlecht.
Everton were indebted to goalkeeper Tim Howard who celebrated his 29th birthday in style with a string of fine first-half saves inside the cold and rainswept Artemio Franchi stadium in Florence. But Fiorentina were deserving winners with second half goals from Serbian striker Serbian Kuzmanovic and midfielder Riccardo Montolivo.
"We were a little too negative and too cautious," admitted Everton skipper Phil Neville. "We didn't play the way we could so it was a let down. But there'll be a great atmosphere at Goodison next Wednesday for the second leg. We'll have to play at a higher tempo, put in crosses and create chances. We need to play like Everton can play."
Tottenham's League Cup final hangover showed no sign of abating as PSV took a 1-0 advantage back to the Netherlands for the second leg next week. Jefferson Farfan punished a horrendous first half mistake from debutant Gilberto to inflict a second successive defeat on Ramos's side since they won the League Cup two weeks ago.
At the Reebok, Bolton saw Sporting Lisbon's Simon Vukcevic crack a stunning equaliser to cancel out Gavin McCann's first-half opener to leave Gary Megson's side facing an uphill struggle in Portugal.
Rangers winCeltic 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 thanks to goals either side of half-time from Gabon international Daniel Cousin and Northern Ireland midfielder Steven Davis.
Former European champions Bayern Munich were the night's most impressive winners cliching 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 on the stroke of half-time.
Marseille, also former European champions, moved closer to the last eight with a 3-1 win over Russia's St Petersburg with former Liverpool striker Djibril Cisse scoring twice for the French side.