One of the best goals of Dimitar Berbatov’s career was not enough to keep Tottenham Hotspur in the Uefa Cup after a brave performance against the leaders of the Dutch League in Eindhoven last night. The Bulgaria striker volleyed home from the edge of the penalty area after 80 minutes to send the tie into extra time, but Juande Ramos’s team could not find a second goal and Pascal Chimbonda’s miss in the penalty shoot-out ended a remarkable run in the competition for the Spanish head coach, who had lifted the trophy in each of the past two seasons with Seville.

Tottenham looked like going through to the quarter-finals when Paul Robinson saved PSV’s second penalty, from Danko Lazovic, a substitute. Jermaine Jenas could have won the tie with the fifth kick, but Heurelho Gomes, the PSV keeper, kept his team alive by saving it. Chimbonda dragged the decisive penalty, his team’s second of the sudden-death stage, well wide, but Ramos did not see a need to offer sympathy to either player. “A player who takes a penalty is courageous and should be congratulated,” Ramos said. “When it comes to the fifth penalty, it’s heads or tails.”

For the second successive season, PSV have eliminated a team from North London from European competition. Arsenal were beaten 1-0 on the same ground in the Champions League knockout stage last season, losing 2-1 on aggregate.

Tottenham had attacked early and often in normal time and PSV, who seemed unsure whether to hang on to their 1-0 advantage from the first leg at White Hart Lane or press forward, presented them with their best chance of the first half after 17 minutes. Carlos Salcido’s misplaced pass was intercepted by Steed Malbranque and the French midfield player sped into the penalty area, but his shot from 15 yards was well wide of the near post. Robbie Keane, unmarked in the centre, was visibly frustrated that he had not been picked out.

Ramos introduced Darren Bent for the second half and the move almost paid off immediately. Malbranque played the ball out to Keane on the left and the Irishman’s first-time cross sped into Bent’s path ten yards from goal. Unfortunately, he failed to make anything like the contact he would have wished and Gomes was able to save with ease.

As Spurs pressed forward, openings came PSV’s way. After 53 minutes, Danny Koevermans let the Londoners off the hook when he scooped the ball harmlessly into the arms of the grateful Robinson from six yards instead of shooting home. Chances for Ibrahim Afellay and Jefferson Farfán were further reminders to Tottenham of the danger of committing too many men forward, but there was little option.

Ledley King was withdrawn in favour of Aaron Lennon as Ramos went for broke and after 72 minutes, Bent chose to pass — poorly — to Keane instead of shooting when well-placed and the chance was gone. Finally, the pressure told as Chimbonda crossed from the right touchline and Berbatov met the ball with a stunning volley from 17 yards out. Bent had a header fingertipped over the bar by Gomes and Jenas blocked a fierce volley from Jason Culina as both teams attempted to settle the match in 90 minutes. Berbatov then volleyed over from closer range than from where he had scored.

PSV, whose match against Ajax at the weekend was postponed as a result of a police strike, should have been fresher in extra time, but Tottenham continued to press for the winner. It looked as if it would come from Malbranque until Gomes pulled off the save of the tie, leaping high to his left to push the ball over the bar. After that, you felt it was not Spurs’ night, and the penalties confirmed it.

“We played well, especially in the second half, and scored the goal,” Ramos said. “We wanted the second, but we didn’t get it.”

PSV Eindhoven (4-5-1): H Gomes – J Kromkamp, D Marcellis, C Salcido, Alcides – J Farfán, E Méndez (sub: O Bakkal, 112min), T Simons, J Culina, I Afellay (sub: B Dzsudzsak, 81) – D Koevermans (sub: D Lazovic, 73). Substitutes not used: B Roorda, M Zonneveld, S Rajkovic, I Aissati. Booked: Simons.

Tottenham Hotspur (4-4-2): P Robinson – P Chimbonda, J Woodgate, L King (sub: A Lennon, 61), Lee Young Pyo (sub: D Bent, 46) – T Huddlestone, D Zokora, J Jenas, S Malbranque – D Berbatov, R Keane (sub: J O’Hara, 86). Substitutes not used: R Cerny, T Tainio, K-P Boateng, M Dawson. Booked: Jenas, King, Malbranque, Huddlestone, Zokora.

Referee: M Trefoloni (Italy).