Rangers' Champions League campaign came to a heartbreaking end on Wednesday when a 3-0 defeat by Lyon meant they failed to complete a British sweep of clubs into the last 16.
Rangers were attempting to join city rivals Celtic as well as English giants Manchester United, Arsenal, Liverpool and Chelsea in the knockout stages but they were undone by the classy French champions who snatched the runners-up spot behind Barcelona in Group E.
Meanwhile, Turkish side Fenerbahce grabbed the final remaining place in the last 16 when a 3-1 win over CSKA Moscow guaranteed them the runners-up place in Group G behind Inter Milan.
PHOTO: AP
In Rome, Manchester United and Roma, who had already secured qualification from Group F, drew 1-1 but the game was overshadowed by fighting between fans before kick-off.
In Group H, Arsenal and Sevilla had also already made sure of going through but the Spanish side finished top with a 3-0 win over Slavia Prague while the Gunners were runners-up after seeing off Steaua Bucharest 2-1.
The night's drama was at Ibrox where Glasgow Rangers only required a draw but a late Olympique Lyon double by Karim Benzema (85 and 88 minutes), which added to Sidney Govou's early opener, proved decisive.
But Rangers were left to rue an astonishing miss from their French striker Jean-Claude Darcheville.
He had the chance to level in the 79th minute but he managed to scoop his shot from inside the six-yard box onto the crossbar with the goal at his mercy.
To complete a miserable night, Darcheville was shown a straight red card in injury time for a foul on Kim Kallstrom.
"It was a disappointing night and a disappointing performance overall," said Rangers coach Walter Smith, whose side will now slip into the UEFA Cup. "I felt Lyon were wilting late in the game but we gave away a bad second goal. We'll play in the UEFA Cup but that's not a consolation at the moment. Maybe it will be in a few days' time."
Ronaldinho returned to scoring form in Europe with a goal in Barcelona's 3-1 win over VfB Stuttgart. Samuel Eto'o was also on target to bag his first goal since his return from injury.
Eto'o, playing only his third match of the season, said his biggest thrill was to feel that he is regaining full fitness.
"It's nice to score, but it's not the most important for me. The crucial thing for me getting back to full fitness after being out so long," the Cameroon striker said.
Fenerbahce qualified for the last 16 for the first time while Italian champions Inter Milan completed their campaign with a 1-0 win at 10-man PSV Eindhoven.
Fenerbahce went a goal down to CSKA Moscow after half an hour when their Brazilian defender Edu diverted a cross from Caner Erkin past his own goalkeeper Volkan Demirel.
But midfielder Alex leveled two minutes later before Champions League debutant Ugur Boral grabbed two goals to put the Turks back on course.
Meanwhile, PSV Eindhoven, who needed to beat Inter Milan to have any hope of qualifying, were reduced to 10 men in the 28th minute when Edison Mendez was red-carded for a foul on David Suazo.
The one-man deficit eventually proved decisive with Julio Cruz scoring his 18th Champions League career goal in the 64th minute to give Inter top spot.
Roma and Manchester United played out an entertaining 1-1 draw in the Italian capital.
United went ahead on 34 minutes when Spanish defender Gerard Pique headed home Nani's corner. But Roma grabbed a point when Mancini levelled in the 71st minute.
"We're satisfied with the performance but I'm disappointed that in the second half we gave possession away and that's how we gave away the goal," United manager Sir Alex Ferguson said.
Fans of both sides clashed just before kick-off. Groups of supporters threw bottles, chairs and tables at each other as fans packed bars close to the Olympic Stadium.
It was also reported that five English fans and one Italian had been hurt in stabbing incidents but none were believed to be seriously injured.
At the Emirates Stadium, Arsenal were forced to settle for second place in Group H despite finishing with a 2-1 win against Steaua Bucharest.
Gunners boss Arsene Wenger was confident his team could survive what could be a tricky next stage.
"We could get a good draw and it could be an interesting last 16," the Frenchman said.
First half goals from Abou Diaby and Nicklas Bendtner put the Gunners in control before Dorel Zaharia replied after the break.
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