Manchester United clinched a place in the last 16 of the Champions League after a Wayne Rooney penalty three minutes from time on his return to the starting line-up for the first time since October sealed a 1-0 win over Rangers at Ibrox here on Wednesday.
The English international had rattled the crossbar with a header and Allan McGregor saved well from Michael Carrick and Dimitar Berbatov as the home side, whose squad was ravaged by injuries, looked to hold on for a point.
However, they will have to settle for the Europa League as Valencia ensured they finished in the top two with victory over Bursaspor.
However Steven Naismith’s foul on Fabio late on presented Rooney with a spot-kick which he smashed past the keeper as the Old Trafford side claimed their fourth win in a row and fifth clean sheet of Group C.
Before the match Walter Smith had promised Rangers would adopt a more attacking approach but a host of injuries to first team stars resulted in a return of the more familiar 5-4-1 formation.
Youngster Kyle Hutton was handed his Champions League debut in a Rangers side that could only field six substitutes.
Rooney returned to partner Berbatov up front as Sir Alex Ferguson made eight changes to the side which drew with Rangers in the first game of the group.
Steven Davis, in an unfamiliar role at right-back, was involved in an early scare for the home side when he appeared to clatter into the back of Berbatov in the box but referee Massimo Busacca waved away his protests.
Minutes later Berbatov was presented with another chance but the Bulgarian’s header from a Fabio cross was straight to McGregor.
Opportunities at the other end were few and far between but Kenny Miller should have done better when David Weir’s knock-on found him at the back post but the Scotland striker headed wide.
A neat passing move saw Carrick play in Nani but the Portuguese international’s shot was high and wide before Rooney silenced the home crowd when his header from a Fabio cross rattled the bar.
Miller blew a golden chance to fire Rangers ahead in the 42nd minute. Naismith sent him clear down the right channel but with Vladimir Weiss lurking at the far post Miller opted to shot from a tight angle which Edwin van der Sar blocked with his legs.
Rooney sent a curling free-kick from 25 yards wide and Berbatov sliced a volley straight to McGregor from a Ryan Giggs cross as the Old Trafford stars began the second-half with an attacking onslaught.
A clever flick from Rooney made room for Carrick but the Englishman’s low drive was well saved by the keeper. The game became to open up and chances fell at both ends.
United failed to deal with Richard Foster’s ball into the box allowing Naismith to poke a shot goal wards but van der Sar made an instinctive fingertip save. Seconds later Berbatov found room in the box but his shot was smartly saved by McGregor.
The Bulgarian then saw a fierce strike blocked by Davis and as Giggs put the ball back into the box Rooney sent a diving header wide from six yards out.
It looked like it wasn’t going to be the Englishman’s night until he put them ahead from the spot in the 87th minute.
Naismith was penalised for a high kick on Fabio and Rooney, plagued with off-field problems this season, stepped up to smash a kick low to the left to send McGregor the wrong way.
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