Rangers 0 Manchester United 1:Wayne Rooney grabbed the winner from the penalty spot as Manchester United booked their place in the last 16 of the Champions League and Rangers crashed out of the tournament.
The striker made his first start since signing a lucrative new five-year deal and marked the occasion with the only goal of the game late on at Ibrox, after United had been frustrated by the Scottish champions for the majority of the game.
United and Valencia will now battle for top spot in Group C in the final game, while Rangers can take some consolation from parachuting into the Europa League ahead of Turkish champions Bursaspor.
United could have had a penalty in the first couple of minutes when Dimitar Berbatov went to ground in the box under pressure from Steven Davis but no award was forthcoming from Swiss referee Massimo Busacca.
The English side were threatening again when Fabio cut inside from the left before picking out Berbatov in front of goal but his header was comfortably gathered by Allan McGregor in the Rangers goal.
Rangers carved out their first real chance when Davis whipped a free-kick into the area where Kirk Broadfoot connected to nod down for Kenny Miller but the striker bulleted his header across the face of goal and wide.
United had plenty of possession but were finding it difficult to break down a stubborn Rangers defence and Nani should have done better when he collected from Michael Carrick only to blast well over from close range.
Rooney then came agonisingly close for the visitors and netting his first goal in open play since March when he met Fabio’s cross only to see his header bounce off the crossbar on the way over five minutes before the interval.
Rangers should have had the net bulging when Miller raced on to a Steven Naismith ball down the right flank and cut inside only to see his six-yard drive blocked at the near post by Edwin van der Sar.
United were out of the traps quickly after the restart and Rooney saw a free-kick from distance curl just past the post, before his close-range header was smothered by McGregor.
Carrick then forced an excellent save from the Rangers goalkeeper as United tried to increase the pressure on their hosts.
But Rangers had a decent chance of their own when Jonny Evans, trying to shepherd the ball back to his keeper, let Naismith in, but Van der Sar was already off his line to make the save as the midfielder tried to poke the ball past him.
At the other end, McGregor was called into action again, this time to prevent a Berbatov shot from finding the back of the net.
Rooney turned provider for Berbatov to have another go but his header was weak and failed to cause any problems for McGregor.
Ryan Giggs then set up Rooney for a diving header but he too spurned the opportunity to open the scoring as the effort fell just wide of the goalkeeper’s right-hand post.
The breakthrough finally came after 87 minutes when Fabio was fouled by Naismith in the box and the referee immediately pointed to the penalty spot. Rooney stepped up and lashed confidently into the bottom corner, leaving McGregor with no chance.