Rangers came agonisingly close to booking a place in the quarter-finals of the Champions League only for their European dream to come to an end at Villarreal.

The Scottish champions had hoped Peter Lovenkrands' 12th-minute strike would provide the win that would see them defy all the odds to progress to the last eight.

But a Rodolfo Arruabarrena leveller just four minutes into the second half saw the Spanish side win the tie on away goals, with an aggregate score of 3-3.

The final season of Alex McLeish's four-and-half-year rein would be tainted with the knowledge that he had failed to deliver any silverware from what had been a dreadful Bank of Scotland Premier League campaign.

However, no matter what happened tonight, McLeish knew he had achieved the European success that had eluded Rangers for so long by taking a Scottish team into the knockout stages for the first time.

But there is little doubt that the cruel nature of their exit from the Champions League will haunt McLeish long after he walks away from Rangers.

He made no fewer than five changes to the side who had narrowly defeated Falkirk at the weekend, with Ian Murray replacing flu victim Steven Smith at right back.

Chris Burke - struck down by the bug last week - started after coming off the bench to impress at the Falkirk Stadium, while Thomas Buffel and Hamed Namouchi shrugged off injuries to take their places in the side.

Lovenkrands was handed the role of lone striker in place of talismanic forward Dado Prso, who was suspended for tonight's game.

Villarreal had also scraped a victory at the weekend, fighting back from behind twice to defeat relegation-threatened Alaves, but they headed into the tie boosted by the knowledge that the last team to leave El Madrigal with a win was Barcelona back in December.

Their biggest concern would have been the amount of Rangers fans who managed to obtain tickets for the match, despite an allocation of just 3,000.

President Fernando Roig had pleaded with Villarreal fans not to sell their tickets to opposition supporters - "polluting a sea of yellow with blue" - but Gers fans were dotted about all four stands.

Rangers knew they had no option but to find the back of the net and Burke and Namouchi both saw early long-range efforts fizz past the post.

Buffel then forced Sebastian Viera into action, after being set up by Lovenrands, but the Villarreal goalkeeper was able to touch just past the post.

Instead, it was Lovenkrands who was destined to earn all the plaudits when he fired Rangers into the lead after just 12 minutes.

Lovenkrands started the move, playing the ball out to Buffel before he threaded into the path of Barry Ferguson.

Viera raced off his line to block, but the ball was cut back to Lovenkrands to rifle home the opener from 12 yards.

Villarreal tried to hit back quickly through Jose Mari but his shot was blocked by Julien Rodriguez, before Diego Forlan nodded a Juan Roman Riquelme free-kick just over.

Ronald Waterreus then pulled a save straight out of the top drawer to deny Forlan the equaliser, after he had been released into the box by Gonzalo.

Villarreal took advantage of the interval to make two changes, Guillermo Franco and Hector Font replacing Jose Mari and Javi Venta.

Rangers, with a precious 1-0 lead to protect, emerged for the second half with the same eleven players.

But the Scottish side were shattered just four minutes after the restart when Villarreal drew level.

Forlan squared across the face of goal and a back flick from Riquelme allowed Arruabarrena to fire home from just outside the six-yard box.

The Ibrox club made their first change of the game after 63 minutes when Buffel made way for Kris Boyd.

But it was Villarreal who almost found the back of the net again when Franco forced Waterreus into another impressive save.

Forlan had been threatening to find the back of the net all night and he came close again when he burst through on goal only to send his chip across the face of goal and past the post.

At the other end of the park, Boyd connected awkwardly with a Burke cross and squandered the opportunity to become an instant hero by firing wide from a few yards out.

Ian Murray then forced Viera into a block at the near post as the clock ticked down but he, like Villarreal in this tie, held firm.

Teams

Villarreal Viera, Javi Venta (Hector Font 46), Rodriguez,Pena, Arruabarrena, Senna, Tacchinardi, Josico,Riquelme (Calleja 85), Forlan, Jose Mari (Franco 45).

Subs Not Used: Barbosa, Guayre, Quique Alvarez, Alcantara.

Booked: Arruabarrena, Viera, Tacchinardi, Franco.

Goals: Arruabarrena 49.

Rangers Waterreus, Hutton, Rodriguez, Kyrgiakos, Murray,Burke (Novo 87), Ferguson, Hemdani, Namouchi,Buffel (Kris Boyd 64), Lovenkrands.

Subs Not Used: Klos, Ricksen, Bernard, Andrews, Gavin Rae.

Booked: Murray, Hutton, Buffel.

Goals: Lovenkrands 12.

Agg (3-3)

Att: 23,000

Ref: Alain Hamer (Luxembourg).