Late Rooney Penalty Sends Rangers Out
A late penalty from Wayne Rooney eased Manchester United into the last 16 of the Champions League, with Rangers dropping into the Europa League.
Rooney converted an 87th-minute spot-kick awarded for Steven Naismith's high challenge on Fabio da Silva.
Rooney had earlier hit the crossbar with a first-half header as United enjoyed the bulk of possession.
Rangers' best chances fell to Kenny Miller but the striker sent a header wide and had a close-range shot saved.
United were far from their best but extended their unbeaten run to 28 games without too much fuss.
Rooney, making his first start since the beginning of October, was rather rusty but demonstrated a few nice touches and slammed the decisive penalty home in emphatic style.
A Rangers side missing Madjid Bougherra, Sasa Papac and Maurice Edu were forced into a defensive reshuffle yet remained compact and obdurate.
However, for a side needing to take three points to have any chance of progress, Walter Smith's men were too timid in attack.
With Steven Davis deployed as a stand-in right-back, Rangers missed his energy and clever promptings in the middle of the park.
And the Northern Ireland midfielder was fortunate not to concede a penalty in the first few minutes when he awkwardly clattered into Dimitar Berbatov.
Soon after, the Manchester United forward was able to connect with a cross from da Silva but could only find the arms of Allan McGregor with a close range header.
Rangers were seldom seen as an attacking force but they were presented with a good chance on 15 minutes when David Weir headed on a deep free-kick from Davis and Miller could only nod wide of the far post from the angle of the six-yard box.
With Rangers content to sit back and United lacking any real sense of urgency there was little action to keep either goalkeeper warm as temperatures plummeted.
A neat United move fizzled out with a Nani mis-hit on the edge of penalty area and the Portuguese winger then blazed over the crossbar after a sharp one-two with Michael Carrick.
Rooney, who was roundly jeered throughout by the home crowd, had been very quiet but went close with a soaring header that crashed against the bar on 39 minutes.
Rangers responded immediately, with Naismith slipping Miller in behind the visiting defence only for the Scotland striker to shoot straight at the legs of Edwin van der Sar from a tight angle.
The second half was less than two minutes old when Rooney whipped a 30-yard free-kick narrowly wide.
Berbatov then made a mess of a volley from near the penalty spot before McGregor got down well to thwart Carrick after a cute lay-off from Rooney had cut the Rangers defence open.
With the game opening up briefly, a misjudgement from United defender Johnny Evans allowed Naismith to get an outstretched toe to the ball on the edge of the penalty area but van der Sar was out quickly to block, while McGregor was again alert to keep out a raking effort from Berbatov.
The Rangers goalkeeper then did well to spread himself and prevent a low Nani delivery from whizzing across his goal.
With the home side remaining reluctant to get men forward, the match appeared to be petering out when da Silva's dart into the penalty box was brought to a crude halt by the high boot of Naismith.
Rooney confidently converted from the spot, with McGregor diving in the opposite direction, to leave Sir Alex Ferguson's side three points ahead of Valencia going into the last round of group fixtures.
Rangers will travel to bottom side Bursaspor knowing third place in the section is already theirs.
Rooney hammered home a late penalty to earn United victory at Ibrox
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