Spurs head coach Juande Ramos’s hopes of winning a third successive Uefa Cup were ended in a penalty shootout as his side lost 6-5 to PSV Eindhoven.

Jermaine Jenas had a chance to win the shootout in Holland but his tame effort was saved by PSV keeper Heurelho Gomes.

Pascal Chimbonda then missed the 14th spot-kick as his effort rolled wide.

Dimitar Berbatov ensured the game went to extra-time and ultimately penalties with a superb second-half volley after Chimbonda swept over a cross.

Everton suffered Uefa Cup heartbreak as they lost to Fiorentina on penalies.

Andrew Johnson’s bundled early goal and Mikel Arteta’s stunning 67th-minute strike drew the tie level as Everton dominated the last 16 tie throughout.

But Fiorentina goalkeeper Sebastien Frey produced a string of brilliant saves to keep Everton at bay.

Yakubu hit the post with his effort in the shoot-out and Frey saved from Phil Jagielka, but Fiorentina hit the target each time for a 4-2 win on penalties.

Jefferson Farfan pounced on an error from Tottenham debutant Gilberto to hand PSV Eindhoven a crucial first-leg lead in their Uefa Cup last-16 match.

The Peruvian took the ball off the Brazilian 25 yards from goal, drove into the box and then fired past Paul Robinson brilliantly on 33 minutes.

It rewarded a fine display from PSV, who could have won by more had Farfan not wasted three other great chances.

Robbie Keane had Spurs’ best effort, but keeper Heurelho Gomes saved well.

Fiorentina produced a stunning display to earn an advantage against Everton in their Uefa Cup last 16 first leg tie.

The Italians dominated for long spells and went in front late on when Zdravko Kuzmanovic slotted home from 20 yards.

They should have already been ahead, Christian Vieri twice denied superbly by Tim Howard, who also parried away another long-range Kuzmanovic effort.

They doubled their lead when Riccardo Montolivo volleyed home after a slick passing move with nine minutes to go.

Bolton earned an invaluable first-leg lead against Spanish giants Atletico Madrid in the last 32 of the Uefa Cup.
The hosts had keeper Jussi Jaaskelainen to thank for keeping the scores level with a world class one-handed save to deny Antonio Lopez on 12 minutes.

But the complexion of the match shifted in Bolton’s favour when Atletico substitute Sergio Aguero was sent off for spitting on 74 minutes.

And moments later El Hadji Diouf fired the winner from six yards.