Wayne Rooney converted a late penalty to send Manchester United FC through to the last 16 from UEFA Champions League Group C and leave Rangers FC facing UEFA Europa League football in the new year.
Starting his first match for United since 26 September, the England striker sent goalkeeper Allan McGregor the wrong way from the spot in the 87th minute after Steven Naismith's high foot had brought down Fabio in the box. Sir Alex Ferguson's side now need a point at home against fellow qualifiers Valencia CF in two weeks' time to top the section, while Rangers are certain of finishing third ahead of their final opponents Bursaspor and entering the UEFA Europa League round of 32.
The opening stages of the match belonged to United, with some neat interplay testing a well-marshalled Rangers defence. The Scottish champions suffered an early fright when Fabio danced past a Naismith challenge and delivered a dangerous cross into the box, but McGregor was equal to the header from Dimitar Berbatov.
Backed by a vociferous crowd, Rangers eventually settled and were unfortunate not to break the deadlock. A Steven Davis free-kick was knocked on by David Weir, only for Kenny Miller to loft his header just wide of the post. Again, though, the visitors ought to have made their dominance count when Rooney turned a Fabio cross onto the top of the crossbar.
Miller found space minutes before the break, yet just as the Ibrox crowd prepared to celebrate, the striker shot straight at Edwin van der Sar from an acute angle. United came out the stronger in the second half and Rooney sent a curling free-kick a metre wide of McGregor's right post, before Berbatov failed to connect with a precise Ryan Giggs cross.
The enthralling duel showed no sign of abating and clever play between Giggs and Rooney presented Carrick with a gilt-edged chance, which McGregor promptly denied with a stunning stop. Van Der Sar then had to be alert to frustrate Naismith, and the game appeared to be heading for a draw until United won a penalty and Rooney – returning from a groin injury and a spell of rehabilitation in the United States – slotted in his first club goal since a 3-0 victory against West Ham United FC on 28 August.