Villarreal win on away goals
Rangers' dream of becoming the first Scottish side in the quarter-finals of the Champions League ended as they lost on the away-goals rule to Villarreal.
Barry Ferguson was distraught at the final whistle
Rangers took an early lead when Peter Lovenkrands drove the ball home from 16 yards at the Estadio el Madrigal.
Ronald Waterreus saved well from Diego Forlan in a rare Villarreal break as Rangers dominated the first half.
But Rodolfo Arruabarrena fired in the equaliser from a Forlan cross and Villarreal held on for the draw.
Olivier Bernard and top scorer Kris Boyd had been dropped from the Rangers side that defeated Falkirk, while Dado Prso was suspended and Stevie Smith missing with flu.
Ian Murray was at left-back, with Hamed Namouchi in midfield and Thomas Buffel and Lovenkrands were up front.
Villarreal were unchanged from the first leg, with midfielder Juan Pablo Sorin still out injured.
Rangers were first to threaten, moving the ball about confidently and dominating possession.
Buffel fired in a drive on the turn from the edge of the box that goalkeeper Sebastian Viera pushed away for a corner.
But the opening goal came after 12 minutes, when the ball broke off Viera as he dived at the feet of Barry Ferguson and Lovenkrands side-footed home from 16 yards.
Peter Lovenkrands opened the scoring for Rangers
Villarreal began to see more of the ball but were rarely threatening.
They did almost make Rangers pay after a free-kick into the home box was cleared.
Forlan broke clear one-on-one with Waterreus, but the goalkeeper blocked the effort superbly with his legs.
Rangers had subdued Villarreal for the opening half but conceded an equaliser four minutes after the break.
Forlan's low, driven cross into the six-yard box beat everyone apart from Villarreal captain Arruabarrena, who side-footed home at the back post.
Sotirios Kyrgiakos missed a good chance to put Rangers straight back in front, the defender scooping the ball over the bar from five yards following a Ferguson free-kick.
Villarreal then took control and a neat ball from Forlan gave Guillermo Franco a chance, but the substitute striker's shot was blocked clear by Waterreus.
Franco then had a free header but sent his attempt straight at the goalkeeper from 12 yards.
Forlan lofted the ball over the bar after another break, while Rangers substitute Boyd failed to connect at the front post after a fine, low cross from Burke.
Rangers pressed forward in the latter stages but Villarreal held out to move into the quarter-finals for the first time in their history.
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.
Goal: 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.
Goal: Lovenkrands 12
Ref: Alain Hamer (Luxembourg)