TOTTENHAM'S hopes of a second trophy this season disappeared in Holland on Wendesday night when they lost 6-5 on penalties to PSV Eindhoven after extra-time in a dramatic Uefa Cup last 16 shoot-out in front of a sell-out 33,000 crowd

TOTTENHAM'S hopes of a second trophy this season disappeared in Holland on Wendesday night when they lost 6-5 on penalties to PSV Eindhoven after extra-time in a dramatic Uefa Cup last 16 shoot-out in front of a sell-out 33,000 crowd.

Jermaine Jenas had a spot-kick to take Spurs through to the last eight but his penalty was brilliantly saved by PSV keeper Heurelho Gomes, who had earlier produced a stunning one-handed save to deny Steed Malbranque in the last minute of extra-time.

However, Pascal Chimbonda then missed the 12th spot-kick, rolling his effort wide and Tottenham were left to think what might have been after Dimitar Berbatov's world-class strike, which took the tie to extra-time.

The Lilywhites, trailing 1-0 from last week's first leg, produced an uninspiring first 45 minutes. However, Juande Ramos, chasing a third successive Uefa Cup after winning the last two with Sevilla, changed things round at half-time.

The Spaniard sent on a third striker, Darren Bent, for former PSV favourite Young Pyo-Lee and moved Didier Zokora to left-back. The changes added urgency to Spurs' play and Bent soon had an effort scrambled away by Gomes after being released by Robbie Keane.

However, Spurs had a let-off at the other end when a cleverly worked free-kick left Danny Koevermans with only Paul Robinson to beat, but the striker shot tamely into the keeper's arms.

Shortly afterwards, a Tom Huddlestone free-kick from the right found Berbatov unmarked, but he glanced a header just wide of the far post.

Ramos made his second substitution just after the hour mark, sending on Aaron Lennon for Ledley King and moving Zokora to the centre of defence.

Then a mix-up between Huddlestone and Zokora allowed Ibrahim Afellay in on goal, but Robinson was equal to the powerful shot.

Spurs survived a Jefferson Farfan curled free kick over the wall to hit back and Bent, having raced into the area, scuffed his shot with Keane unmarked. A minute later the Irishman looped a header onto the roof of the net.

However, Tottenham's pressure finally yielded a goal - and what a goal - nine minutes from time. Bent's header set up Chimbonda and the full back's excellent cross was majestically volleyed home by the Bulgarian.

Spurs now sensed glory. With young Jamie O'Hara on for Keane, they almost got it when Bent's goal-bound header from Lennon's cross was tipped over by the PSV keeper.

And so to extra-time. Bent nearly scored early in the first period, replicating Berbatov's glorious volley after being sent clear by the Bulgarian. The second period ended with Gomes denying Malbranque with that magical tip over save.

In the penalty shoot-out, Robinson saved the second PSV penalty from Danko Lazovic and with Berbatov, O'Hara, Huddlestone and Bent all scoring, Jenas had to the chance to be Spurs hero.

He missed and although Zokora blasted in his spot-kick - his first ever goal for Spurs - Chimbonda's nerve failed and Tottenham were out.