Rangers 0-1 Man Utd
Manchester United took the spoils in the Battle of Britain courtesy of a goal from Phil Neville.
Neville struck after less than five minutes to give United the three points that sees them move ahead of their Group E opponents.
But Rangers can consider themselves unfortunate to have finished on the losing side after more than matching Sir Alex Ferguson's team throughout.
There were 50 arrests before and during the game for minor public
order offences, but a police spokeswoman said the game had passed off with relatively little incident.
It was the first time Ferguson had come face-to-face with Scottish opponents in a competitive match during his time as United boss.
The home fans more than made up for the absence of a Scot in the Rangers line-up, creating a deafening atmosphere at a sell-out Ibrox.
United defender John O'Shea clattered into Peter Lovenkrands after 35 seconds and earned himself a booking from the referee, raising the noise level by another notch.
But it was the away fans who had something to shout about inside five minutes when Neville gave United a shock lead.
Neville picked up a pass from Ruud van Nistelrooy, was allowed almost a free passage into the box and evaded some half-hearted challenges before slotting past Stefan Klos.
Despite the early setback Rangers kept their composure and continued to probe for openings in the United defence.
Opportunities came their way and Michael Ball's cross found the head of Lovenkrands, who outjumped O'Shea but could not keep his header below the bar.
5 mins: Phil Neville gets United off to a flyer
43 mins: Silvestre had a header cleared off the line
80 mins: Lovenkrands flashes a fraction wide of Howard's upright
Paolo Vanoli should have scored when the ball fell kindly at his feet after Lovenkrands' header and Fernando Ricksen's follow-up shot were blocked.
But with time to pick his spot, Vanoli sliced his left-foot shot horribly wide of the near post.
Rangers ended the first period well on top and Shota Arveladze was a whisker away from an equaliser, but his shot was somehow kept out by Tim Howard's fingertips.
United could have added a second completely against the run of play when Mikael Silvestre got his head to a Ryan Giggs corner and Mikel Arteta cleared off the line.
There was no holding back in the second half and both sides had chances to add to the scoreline.
Van Nistelrooy shot wide from a good position and then Roy Keane's powerful effort from the edge of the box tested Klos.
At the other end Craig Moore had a header cleared off the line by the increasingly influential Phil Neville.
Michael Mols released Lovenkrads but Rio Ferdinand got back to make a brilliant last-ditch tackle.
From the resulting corner Lovenkrands found space to power in a header that Howard did well to hold.
Lovenkrads flashed a shot across the face of the goal and Christian Nerlinger was denied by Howard as Rangers ran out of luck and out of time.
Rangers: Klos, Khizanishvili (Ross 86), Berg, Moore, Ball,
Ricksen, Arteta, Vanoli (Nerlinger 67), Lovenkrands, Arveladze,
Subs not used: McGregor, Emerson, Ostenstad, Capucho, Hughes.
Man Utd: Howard, Gary Neville, Ferdinand, Silvestre, O'Shea,
Phil Neville (Butt 85), Keane, Scholes,
Fortune (Djemba-Djemba 90), Van Nistelrooy, Giggs.
Subs not used: Carroll, Ronaldo, Bellion, Forlan, Fletcher.
Booked: O'Shea, Scholes.
Referee: Anders Frisk (Sweden)