Villarreal 1 Rangers 1 <i>(Villarreal win on away goals)</i>: Villarreal end Rangers' dreams of final triumph for McLeish

Rangers came agonisingly close to booking their place in the quarter-finals of the Champions' League only for their European dream to come to an end in Villarreal last night, after Peter Lovenkrands' 12th-minute strike had promised to provide the win that would have allowed Alex McLeish's side to defy the odds and 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 players are shattered - they gave everything," McLeish said. "We had some great chances to get one of the most historic results in Rangers' history. I am very proud of the players' performance - their discipline and composure. It's the proudest I've been without a doubt."

The Danish striker Lovenkrands gave Rangers an ideal start, firing past Sebastian Viera. But Villarreal put Rangers under pressure after Sotirios Kyrgiakos fouled Diego Forlan. Juan Roman Riquelme flighted a free-kick into the box only for Forlan to nod past Ronald Waterreus and over the bar.

Rangers were shattered just four minutes after half-time when the Spaniards drew level. Forlan crossed and a back-heel from Riquelme allowed Arruabarrena to fire home from just outside the six-yard box.

Villarreal then went in search of a goal to kill off Rangers, narrowly missing out when Guillermo Franco twice forced Waterreus into impressive saves.

The build-up to the match was marred when a group of ticketless Rangers' fans hurled bottles at the Villarreal bus as it arrived.

Villarreal (4-4-2): Viera; Javi Venta (Hector Font, h-t), Rodriguez, Pena, Arruabarrena; Senna, Tacchinardi, Josico, Riquelme; Forlan, Jose Mari (Franco, h-t). Substitutes not used: Barbosa (gk), Guayre, Calleja, Quique Alvarez, Alcantara.

Rangers (4-5-1): Waterreus; Hutton, Rodriguez, Kyrgiakos, Murray; Burke, Ferguson, Hemdani, Namouchi, Buffel (Boyd, 63); Lovenkrands. Substitutes not used: Klos (gk), Ricksen, Bernard, Andrews, Novo, G Rae.

Referee: A Hamer (Luxembourg).

* Juventus progressed to the quarter-finals, beating Werder Bremen 2-1 in Turin. Goals from David Trezeguet and Emerson two minutes from time secured a win on away goals after a 3-2 defeat in the first leg.