UEFA CUP PSV Eindhoven 0 Tottenham 1 (PSV wins on penalties 6:5)
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 tonight.
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 cancelled 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 Barclays Premier League side.
Tottenham head coach Juande Ramos was given an introduction to English penalty shoot-out heartache as his UEFA Cup hat-trick dream ended against PSV Eindhoven.
Asked if he knew of the history of English teams losing their nerve in shoot-outs, Ramos said: 'I didn't know about it. When it comes to the fifth penalty it's heads or tails. That is how it is with penalties.'
Ramos has a reputation of being meticulous but is understood not to practice penalties in training.
'Every player in the Premier League is capable of scoring a penalty but in a situation like this you cannot train the pressure that comes with it,' he said.
'Everyone is sad in the dressing room but every player that takes a penalty is courageous, I can only congratulate them.'
Ramos changed his formation a number of times as Spurs chased the goal to cancel out PSV's one-goal advantage from the first leg.
Firstly he went with a narrow midfield, meaning Aaron Lennon was on the bench, then he played with three strikers for the start of the second half when he brought on Darren Bent.
'I don't regret not playing with Bent from the start, in the second half we played well, we wanted a goal and got it,' Ramos said.
Steed Malbranque wasted the only real chance of the first half, then Bent's arrival put pressure on the hosts.
Danny Koevermans did fluff an easy chance for PSV and Paul Robinson was tested, but Berbatov's strike sent the tie into an extra period.
The Bulgaria striker met Chimbonda's cross with a first-time volley that left Gomes with no chance. Ramos was only interested in his performance.
'He played a good match but I don't think it is his best match since I've been at Spurs,' he added.
Malbranque had a volley saved that could have won it, then in the shoot-out Robinson saved early on. Jenas could have won it, then Chimbonda went wide.
'We don't regret anything, we wanted to win the game and we won it, then penalties is like a lottery,' Ramos said. 'We didn't score the fifth penalty, if we scored that we would have been through.
'We have two months so I think they have to do their best. They need to get themselves together and charge up.'
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 cancelled 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 Barclays Premier League side.
Tottenham head coach Juande Ramos was given an introduction to English penalty shoot-out heartache as his UEFA Cup hat-trick dream ended against PSV Eindhoven.
Asked if he knew of the history of English teams losing their nerve in shoot-outs, Ramos said: 'I didn't know about it. When it comes to the fifth penalty it's heads or tails. That is how it is with penalties.'
Ramos has a reputation of being meticulous but is understood not to practice penalties in training.
'Every player in the Premier League is capable of scoring a penalty but in a situation like this you cannot train the pressure that comes with it,' he said.
'Everyone is sad in the dressing room but every player that takes a penalty is courageous, I can only congratulate them.'
Ramos changed his formation a number of times as Spurs chased the goal to cancel out PSV's one-goal advantage from the first leg.
Firstly he went with a narrow midfield, meaning Aaron Lennon was on the bench, then he played with three strikers for the start of the second half when he brought on Darren Bent.
'I don't regret not playing with Bent from the start, in the second half we played well, we wanted a goal and got it,' Ramos said.
Steed Malbranque wasted the only real chance of the first half, then Bent's arrival put pressure on the hosts.
Danny Koevermans did fluff an easy chance for PSV and Paul Robinson was tested, but Berbatov's strike sent the tie into an extra period.
The Bulgaria striker met Chimbonda's cross with a first-time volley that left Gomes with no chance. Ramos was only interested in his performance.
'He played a good match but I don't think it is his best match since I've been at Spurs,' he added.
Malbranque had a volley saved that could have won it, then in the shoot-out Robinson saved early on. Jenas could have won it, then Chimbonda went wide.
'We don't regret anything, we wanted to win the game and we won it, then penalties is like a lottery,' Ramos said. 'We didn't score the fifth penalty, if we scored that we would have been through.
'We have two months so I think they have to do their best. They need to get themselves together and charge up.'
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