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 last night.
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.
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.
Paul Robinson saved Danko Lazovic's spot-kick but Mario Gomes also saved from Jenas and Chimbonda shot wide to send PSV through.