Manchester United qualified for the last 16 of the UEFA Champions League after a late penalty from Wayne Rooney gave them a 1-0 victory over Rangers who dropped into the Europa League.

Rooney, who had earlier hit the crossbar with a first half header, smashed home the penalty in the 87th minute after Naismith's high legged challenge on Fabio. Rangers had chances themselves, with Kenny Miller guilty of missing twice - first with a header sent wide and then with a close range shot.

The win means United extend their unbeaten run to 28 games, though they were far from their best against a Rangers side who were without the services of key defenders such as Madjid Bougherra, Sasa Papac and Maurice Edu.

Rangers' manager Walter Smith had surprisingly set themselves up in a formation with a 5 man defense despite needing a win to harbor hopes of qualification into knock-outs.

The game opened with penalty shouts from United after Davis, employed at right back due to the defensive reshuffle, brought down Berbatov in the box within the first couple of minutes. Fortunately for the Northern Island midfielder, the referee decided against a spot kick.

Berbatov was again involved minutes later when he headed Fabio's ball straight into the hands of the keeper Allan McGregor from close range.

Rangers had to make use of their set pieces to get anything off the game, and they came close when on 15 minutes, David Weir headed on a deep free-kick but Miller in the six yard box headed it wide of the far post.

With both teams lacking urgency, chances were few and far between. The closest United came to a goal in the first half was when Rooney crashed a header onto the cross bar in the 39th minute.

At the other end, Naismith slipped in Miller behind the United rear-guard only to see the striker shoot straight at the legs of Edwin van der Sar from a tight angle when he had the option of teeing up two of his onrushing teammates.

The second half was slightly more open with Berbatov and Carrick seeing their chances wasted, while Naismith had his attempt saved by Van der Sar at the other end.

The match appeared to be headed to a goalless draw with neither team committing enough men forward. However, when Fabio's venture into the box was blocked by the high leg of Naismith, the referee had no option but to point to the spot.

Wayne Rooney stepped up and slammed the ball to his left corner sending McGregor the wrong way leaving United in prime position to qualify as group winners. Their meeting with Valencia in the next match-day fixture will decide the winner.