Wayne Rooney’s emphatically-struck late penalty proved the difference between the sides as Manchester United qualified for the Champions League knock-out stages and consigned their Scottish opponents to the Europa League.

United dominated possession throughout, but the game was drifting towards a 0-0 draw when United left-back Fabio da Silva was felled by a high, reckless penalty box challenge by Steven Naismith in the 86^th minute.

Rooney, who was booed all night by the home crowd, sent keeper Allan McGregor the wrong way from the spot.

United could have had a second-minute penalty when Rangers’ Steven Davis felled Dimitar Berbatov. And United came closest to scoring in the first half when Rooney leapt prodigiously to head Fabio’s 39^th-minute cross against the crossbar.

But Kenny Miller had two good chances for the hosts, heading David Weir’s knock-down wide on 16 minutes and firing at United keeper Edwin Van der Sar from close range three minutes before the break.

The second half was more open but all the best chances fell to United, McGregor saving well from Michael Carrick, Berbatov and Fabio.

However, Fabio’s header came a split second before Naismith’s flying tackle and McGregor’s fine left-handed save was rendered irrelevant by Rooney’s penalty.