Juande Ramos’ dream of a UEFA Cup hat-trick ended despite a stunning Dimitar Berbatov volley as Tottenham crashed out on penalties against PSV Eindhoven in Holland .

Ramos has endured a few scares winning the competition with Sevilla in the past two seasons – goalkeeper Andres Palop scored at this stage a year ago – and this time Berbatov came to his rescue.

The Bulgarian’s ferocious drive canceled out PSV’s advantage from the first leg before the shoot-out, with PSV earning a place in the quarter-finals after Jermaine Jenas and Pascal Chimbonda failed from the spot.

Ramos tried everything to get the better of PSV but his luck in this competition finally ran out.

The Spaniard won the first of his UEFA Cups by defeating Middlesbrough at Eindhoven’s ground and although he wanted a repeat performance from Spurs, the first leg at White Hart Lane suggested it would never be as one sided.

Ramos’ way around the stubborn Dutch champions was attempting new formations, starting with Didier Zokora as a holding midfielder and Jenas, returning from a twisted ankle picked up in the first leg, part of a trio in the centre.

The narrow approach meant there was no room for winger Aaron Lennon, who has been rested under Ramos twice but never dropped.

Earning a reputation as a man cannot be second-guessed, Ramos also brought Young-Pyo Lee in at left-back for his first appearace since Janaury.

Ramos spoke on the eve of the match about how the South Korea full-back had fallen down the pecking order – but under the Spaniard only the unpredictable can be expected.

When the new formation did not yield success, Ramos changed it again and again until Spurs were back in the match, although it did take Berbatov’s moment of magic.

PSV had last weekend to rest after a police strike meant their clash against Ajax was called off, but their fresh players were hardly making the running and their most effective man was midfield destroyer Timmy Simons.

Berbatov created Spurs’ first genuine chance when he charged down a clearance from Carlos Salcido. The ball was squared to Steed Malbranque but the finish was just wide of Gomes’ near post.

From a corner, taken by Jenas, skipper Ledley King was found at the near post and flashed a header across the face of Gomes’ goal – but it was a frustrating first half for Spurs.

Jenas picked up a booking for a trip on Jason Culina, ruling him out of Spurs’ next European game, while King picked one up for a foul on former Liverpool full-back Jan Kromkamp.

Things changed for Spurs at the break when Ramos altered his tactics. He brought on Darren Bent for Lee, and the substitute wasted a glorious opportunity within two minutes.

Robbie Keane was slipped through by Malbranque and supplied a reverse pass – but Bent’s shot lacked power and Gomes was able to claim at the second attempt.

PSV had an even better chance in the 55th minute. They fooled Spurs with a short free-kick and Culina chipped into the danger area. Offside players ran backwards, allowing Danny Koevermans a sight of goal from five yards out – but he miskicked his effort.

Berbatov got on the end of Tom Huddlestone’s free-kick but glanced his header wide, before King was replaced by Lennon.

With the game opening up, Paul Robinson had to save at full-stretch from Ibrahim Afellay after a mix-up between Jenas and Zokora offered a chance. He would have had little chance if Jefferson Farfan’s free-kick had not curled just wide.

Spurs then started going for broke. Bent raced through but squared to Keane rather than taking a shot himself.

Keane then looped a header over the crossbar and almost took advantage when Gomes decided to chest a ball rather than use his hands – but PSV were able to clear.

It was Berbatov’s moment of brilliance, in the 82nd minute, which sent the game into extra-time. He met Chimbonda’s driven cross with a first-time volley on the edge of the area that left Gomes with no chance.

Berbatov could have won the game with a volley in extra-time, as could Malbranque, but it went to penalties – and ended in heartbreak for the Premier League side.

Robinson saved Danko Lazovic’s spot-kick but Gomes also saved from Jenas and Chimbonda went wide to send PSV through.

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