Leeds' crisis season plumbed new depths as David O'Leary's side crashed out of the UEFA Cup to reigning Dutch champions PSV Eindhoven.

Extra time seemingly beckoned in the return leg of this fourth-round clash after Leeds had spurned a series of opportunities, but in the 90th minute Jan Vennegoor of Hesselink pounced on a Theo Lucius shot which had rebounded off the crossbar.

It was enough to give PSV a narrow 1-0 aggregate win at Elland Road, leaving Leeds with nothing more now than 11 Premier League matches in which to avoid the threat of the Intertoto Cup.

O'Leary's stars certainly played with the dawning realisation next season could start in mid-July and with the dreaded prospect of the much-maligned tournament as they wore their hearts on their sleeves.

Such was the cut and inventive thrust of Leeds' football, the tie should have been out of PSV's reach by the interval, only for the United players to head into the break wondering how they had failed to find the net.

PSV coach Erik Gerets had lauded Leeds following last week's goalless first leg in Eindhoven, describing their organisation as "perfect" and claiming O'Leary's side had showed just how an away game in Europe should be played.

If that was the case, Leeds also gave a perfect home performance during the first 45 minutes - all that was lacking was the all-important goal as their recent drought continued to haunt them.

The tone was set after just 85 seconds with a poor defensive clearance falling to Eirik Bakke for a 20-yard half-volley which whistled narrowly over the bar of keeper Patrick Lodewijks.

A repeat performance followed in the sixth minute, this time with Bakke's powerful drive comfortably saved by Lodewijks, who celebrated his 25th birthday last Thursday.

What followed was a series of attacks, with Lodewijks superbly denying Mark Viduka in the 12th minute, racing off his line to block the Australia international's point-blank chip after he seized on a through ball from Lee Bowyer.

It was a brilliant one-two in the PSV area between Viduka and Harry Kewell which came close to unlocking the visiting defence eight minutes later, with the latter's curl on an angled 15-yard shot almost sneaking inside Lodewijks' left-hand post.

The most gift-wrapped of the chances came midway through the half after Viduka had been set free down the right by a raking pass from Danny Mills.

Smith just failed to turn home the striker's goalline pull back, before Kewell was left looking to the heavens for inspiration after blazing his shot over the bar from eight yards with the net gaping.

Lee Bowyer then dragged a 15-yard effort wide after creative approach play by Viduka and Kelly, while Kewell headed over when well placed before PSV finally created their first chance in the 34th minute.

Andre Ooijer narrowly headed wide a Mark van Bommel cross, and when Lucius saw a drive from the edge of the area deflected an inch past Nigel Martyn's left-hand post, the initiative appeared to have been lost.

But Leeds finished the half in the ascendancy, only for Lodewijks to have the final say in denying Smith and Bakke before continuing his stunning form early in the second period in turning aside Bowyer's flicked header.

Nigel Martyn was not to be outdone as he brilliantly tipped away a crisp drive from Matej Kezman after being set up by Vennegoor of Hesselink and van Bommel, the subject of Arsenal's interest but looking anything but a £15million player.

Skipper Rio Ferdinand then twice bravely blocked shots from Kasper Bogelund and Vennegoor of Hesselink as PSV stepped up the pace after growing in confidence from Leeds' failure to score, compounded as Bowyer and Smith then wasted further efforts soon after.

With 15 minutes remaining, Martyn was beaten by Vennegoor of Hesselink, whose first touch set up the opening but whose eventual shot flashed through the six-yard box.

It was merely the prelude to heartbreak for Leeds for with extra time looming the killer blow arrived with seconds of the 90 minutes remaining.

Van Bommel was the provider with a through ball for Lucius to flick his shot onto the bar, and as it dropped inside the six-yard box, there was Vennegoor of Hesselink to make a name for himself by heading home from no more than a yard.

In a moment of controversy it appeared Dominic Matteo, who had followed Vennegoor into the net, then appeared to punch the PSV striker in the face.

However, it was simply frustration from the Leeds centre-back as a different camera angle showed he had merely thumped the ground in frustration as Leeds' miserable run continues.

O'Leary's side are still without a win since New Year's Day, a run of nine games, while they have failed to score in five of their last six matches and are without a goal now for five hours.

Teams:

Leeds: Martyn, Mills, Ferdinand, Matteo, Harte, Kelly, Bowyer, Bakke, Kewell, Smith, Viduka.

Subs Not Used: Robinson, Keane, McPhail, Wilcox, Duberry, Batty, Burns.

Booked: Kelly.

PSV: Lodewijks, Bogelund, Ooijer, Hofland, Bouma, Rommedahl, Vogel, van Bommel, Lucius, Vennegoor of Hesselink (Gakhokidze 90), Kezman.

Subs Not Used: Coutinho, Faber, Ramzi, de Jong, Addo, Nikiforov.

Booked: Bouma.

Goals: Vennegoor of Hesselink 90.

Agg (0-1) Att: 39,755

Ref: Antonio Jesus Lopez Nieto (Malaga).