PSV Eindhoven edged into the UEFA Cup quarter-finals on penalties despite Tottenham Hotspur FC fighting back to level the tie away from home.
Spurs coach Juande Ramos won the UEFA Cup for the last two seasons with Sevilla FC and had been victorious in 12 consecutive two-leg European ties, with a 13th on the cards when Dimitar Berbatov struck late to force extra time and Paul Robinson saved PSV's second penalty from Danko Lazović. But Heurelho Gomes stopped Jermaine Jenas's potentially winning spot-kick and after teenager Dirk Marcellis nervelessly converted, Pascal Chimbonda put Tottenham's seventh attempt wide.
Ramos gave a first start since January for former PSV left-back Lee Young-Pyo and Tottenham quickly moved forward in search of the goal they needed. On 17 minutes Steed Malbranque shot wide after good work from Tom Huddlestone, and the Frenchman then sent through Robbie Keane only for the striker to be denied by a superb Marcellis tackle. Ledley King headed a Jenas corner just past the post, but PSV made it to half-time without conceding.
Although Ramos introduced Darren Bent for Lee before the second half and the striker quickly forced Gomes to save, the home team were beginning to create chances of their own as Spurs reduced numbers in defence. Danny Koevermans latched on to a Jason Culina ball but could not beat Robinson, who also denied Ibrahim Afellay.
Spurs did not give up and Berbatov tested Gomes with a low drive before levelling the tie with nine minutes left, a superb volley from the edge of the box turning in Chimbonda's perfectly-placed cross. PSV sent on Balázs Dzsudzsák and he immediately made Robinson save an angled shot, while Méndez went close and Gomes did superbly to tip over from Bent.
Extra time was a tight affair though Bent's effort was not far off and Gomes tipped away a Malbranque volley. But in the shoot-out it was PSV who prevailed – just – to keep alive their chances of repeating their UEFA Cup success of 30 years ago and end Ramos's personal grip on the trophy.