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.