Rangers' European adventure was brought to an end tonight as they were sent crashing out of the UEFA Cup by Osasuna at the Reyno de Navarra stadium in Pamplona.

Pierre Webo scored the only goal of the match to secure the Spanish side a 2-1 aggregate victory, ending Gers' hopes of gracing this year's final, which will be held at Hampden Park in Glasgow.

Walter Smith's side were always up against it having only managed a 1-1 draw from the home leg of this last-16 tie, while they were also without influential captain Barry Ferguson through suspension.

History was also against the Ibrox club, with no Rangers side ever having managed to beat a Primera Liga team in Spain in eight previous attempts.

Osasuna, who had never reached the quarter-finals of a European competition before, were quickly out of the blocks and they dominated the opening 40 minutes.

Bernardo Romeo had the first chance inside the opening minute after being put through on the left hand-side of the Rangers area by Webo.

However, his left-footed finish was poor and Allan McGregor was untroubled in the visiting goal.

A clumsy challenge from Ian Murray then saw Osasuna win a free-kick 25 yards out, but fortunately for the Light Blues Juanlu's resulting effort flew a yard over the bar.

Rangers briefly threatened in the eighth minute, but Charlie Adam's free-kick on the edge of the box was cleared away.

Osasuna were back on the attack in the 12th minute with a Juanlu cross-shot that flew dangerously across the face of goal, while Gers defender Alan Hutton picked up the first booking of the game for a foul earlier in the Spanish side's move.

Juanlu was seeing plenty of the ball early on and he saw one cross grabbed by McGregor before then having a close-range shot crucially blocked by Hutton after the Rangers defence had given away possession.

Osasuna's domination was total and they really should have taken the lead in the 29th minute when a free-kick found Juanlu totally unmarked on the penalty spot.

However, he was leaning back while attempting to shoot and the effort was screwed wide of goal.

McGregor was called on to stop Enrique Corrales' 25-yard effort, before Rangers finally threatened with headers from David Weir and Adam.

Osasuna were back on the attack at the start of the second half though and the home side felt they should have had a penalty when a cross struck Murray's outstretched arm - however, Danish referee Claus Bo Larsen waved play on.

Rangers responded to that by fashioning their best chance of the match.

Rae robbed Javad Nekunam of possession before powering his way into the Osasuna area - but just as the Rangers captain looked set to slot home, his shot was blocked.

Rangers coach Smith made his first change of the match soon after that, bringing on winger Chris Burke for Kevin Thomson.

In the stands riot police entered the area where the Rangers fans were seated, separating them from the Osasuna supporters sitting nearby.

The riot police had stood in a line in front of the visiting fans for around 10 minutes before an incident then saw the police wade in among the Rangers support, scattering the fans.

Despite bringing on Burke, it was still Osasuna who were looking the more likely scorers and Romeo just failed to get his head on the end of a superb cross into the area.

A poor free-kick from Adam then saw Rangers miss an opportunity to put some pressure on the Osasuna backline, before Dado Prso was sent on to boost the Light Blues attack.

Prso barely had any time to make an impact though before Webo put Osasuna ahead with 20 minutes remaining.

The Rangers defence failed to cut out a cross from the right and Webo latched on to the loose ball at the far post to fire a low shot past McGregor.

McGregor tried his best to keep the ball out, but he could not get enough of his body behind the shot as it flew off him into the bottom corner.

With his side seeing their UEFA Cup hopes slipping away, Smith made another attacking change, sending on top scorer Kris Boyd with around 18 minutes to go.

Ehiogu then had a brief glimpse of goal as a long free-kick somehow found its way through to him, but the veteran defender could not get his foot onto the ball when any sort of connection would surely have resulted in a goal.

Ehiogu was sent up front in the closing stages as Rangers desperately sought a breakthrough, but they could not fashion anything as Osasuna held on for a deserved victory.

Teams

Osasuna Ricardo, Cruchaga, Javier Flano, Corrales, Josetxo,Punal, Juanlu (Juanfran 82), Azpilicueta (David Lopez 66),Nekounam, Romeo (Raul Garcia 74), Webo.

Subs Not Used: Elia, Cuellar, Soldado, Munoz.

Booked: Corrales, Webo.

Goals: Webo 71.

Rangers McGregor, Weir, Ehiogu, Murray, Hutton, Adam,Rae (Boyd 73), Thomson (Burke 53), Hemdani, Sebo (Prso 64),Novo.

Subs Not Used: Klos, Sionko, Svensson, McMillan.

Booked: Hutton, Ehiogu.

Agg (2-1)

Att: 19,126

Ref: Claus Bo Larsen (Denmark).