Penalty heartbreak for Spurs

Spurs lost a dramatic penalty shootout to crash out of the UEFA Cup in Holland this evening.

Pascal Chimbonda was the unlucky player to miss the crucial spot kick, the hosts eventually triumphing 6-5 on penalties.

It was cruel on Tottenham who were the better team on the night, Dimitar Berbatov volleying in the only goal of the game nine minutes from time.

The Lilywhites finished stronger, but could not force a winner in extra time, which meant the lottery of penalties was required to settle this tense contest between two well-matched sides.

The game started slowly, with no chances for either side in the opening stages.

Both teams were guilty of giving the ball away too easily.

The first effort came on 17 minutes, Berbatov laying the ball inside to Steed Malbranque, who drove wide when he should have at least forced the keeper into a save.

It was not the explosive start many expected and the pace was almost pedestrian at times.

Ten minutes before the break, Ledley King rose at the near post, but his header from a corner flashed across the face of the goal and wide.

Jermaine Jenas received a yellow card for a late challenge, before Tom Huddlestone saw a free-kick deflected off the wall for a corner.

Huddlestone then saw a low drive finish just the wrong side of the post, the ball again coming off a defender.

Tottenham were doing all the pressing, though the home keeper never had a save to make in the first half.

PSV were content to sit back and play on the break, but they never came close to testing Paul Robinson in what was a dire opening 45 minutes.

The referee obviously agreed and did not even play a minute of stoppage time.

Tottenham boss Juande Ramos brought on striker Darren Bent for defender Lee at the interval, fully aware that his side would be out unless they scored.

And Bent almost struck within two minutes, his shot from a Robbie Keane centre pushed away by the keeper. It was the first save of the match.

PSV should have struck with their first opening of the game on 53 minutes, Kouvermans failing to control a chip into the box. The striker was onside and unmarked inside the six-yard area. He should have buried the chance.

A Mendez free-kick just cleared Robinson's bar a couple of minutes later, as the hosts at last started to threaten.

At the other end, a Berbatov glancing header from a free-kick went just wide.

Ramos replaced skipper King with Aaron Lennon on the hour, the Spaniard going for broke.

MIdway through the half, Kouvermans forced Robinson to parry a shot from the edge of the box, while Farfan, scorer of the first leg's only goal, curled a free-kick inches over.

It was a far better second half, with both sides now looking capable of breaking the deadlock, Huddlestone driving wide from distance for Spurs.

Bent almost set up Keane, but the latter could not reach the ball with the goal gaping. The Irishman then saw a looping header finish on the roof of the net.

A mix-up between PSV keeper Gomes and defender Salcido almost presented Keane with another chance, but the Dutch hosts got away with it.

The equaliser finally came nine minutes from time, Berbatov volleying a Pascal Chimbonda cross first time into the corner from the edge of the box. It was a cracking strike.

Mendez almost responded for PSV five minutes from time, his drive sailing just past the upright, but it was Spurs who were finishing the stronger, Bent seeing Gomes tip over a header.

The first chance of extra time fell to Bent, who peeled away from his marker and hit a first-time volley just wide.

A Culina volley at the other end appeared to be heading in, before Huddlestone headed it out for a corner.

Berbatov then fired over after a Jamie O'Hara free-kick was deflected into his path.

With a minute of extra time to go, Gomes pulled off a superb flying save to keep out a Malbranque volley, sending the game into a penalty shootout.

SPURS (4-4-2): Robinson; Chimbonda, Woodgate, King (Lennon 60), Lee (Bent 45); Huddlestone, Zokora, Jenas, Malbranque; Keane (O'Hara 85), Berbatov.

Penalty shootout . . .

PSV: Simons sends Robinson the wrong way (1-0 PSV).

Spurs: Berbatov finds the corner (1-1).

PSV: Lazovic sees Robinson save his kick (1-1).

Spurs: O'Hara finds the net, but Gomes gets a hand to it (2-1 Spurs).

PSV: Farfan sends Robinson the wrong way (2-2).

Spurs: Huddlestone sends Gomes the wrong way (3-2 Spurs).

PSV: Salcido finds the corner (3-3).

Spurs: Bent blasts the ball into the corner (4-3 Spurs).

PSV: Uzschack slots it into the corner (4-4).

Spurs: Jenas sees Gomes pull off a flying save (4-4).

PSV: Bakkal puts the ball into the top corner (5-4 PSV).

Spurs: Zokora smashes the ball home (5-5).

PSV: Marcellis sends Robinson the wrong way (6-5 PSV).

Spurs: Chimbonda misses the target. (6-5 PSV).