Rangers 0 Malmo FF 1:Rangers' Champions League hopes were left hanging in the balance tonight after they suffered defeat to Swedish outfit Malmo at Ibrox.
Daniel Larsson grabbed the only goal of the first leg of the third qualifying round tie, leaving the Scottish champions with a major hurdle to overcome in next week's away leg.
It was another frustrating encounter for Ally McCoist, with the new Rangers manager still to secure his first competitive victory at the Light Blues helm.
Lee Wallace was handed his Rangers debut from the start, while skipper David Weir made his first appearance of the season after sitting out Saturday's Clydesdale Bank Premier League opener against Hearts through suspension.
Before the match kicked off, fans were warned about the repercussions of any sectarian singing, having already been banned for next week's return leg in Sweden after being found guilty of discriminatory chanting in European matches last season.
Rangers failed to heed Malmo's early warning signs of attacking intent and the Swedes surged into the lead after 18 minutes.
The move began when Steven Whittaker was robbed of possession by Durmaz and the ball was eventually laid on by Figueiredo to Larsson, who rifled an unstoppable drive past the grasp of McGregor.
The mood was lifted at half-time when new signing Dorin Goian - unable to feature in tonight's game as he awaits a work permit and international clearance - was paraded on the pitch to enthusiastic applause during the break.
Rangers emerged for the second half eager to haul themselves back into the tie but it was Malmo who almost had the net bulging again just a few minutes after the restart.
Papac was cautioned for tripping Larsson before Figueiredo's curling free-kick was tipped one-handed over the crossbar by a full-stretch McGregor. Agon Mehmeti then sent a header flashing narrowly wide of the upright from the corner.
Rangers should have been back on level terms when Nikica Jelavic whipped a tempting ball into the path of Steven Naismith, who should have buried the shot from close range, but he connected on his weaker foot and mis-kicked wide instead.
Naismith had the chance to make amends just moments later in what was a carbon copy of the previous move and, unfortunately for him, the finish was just as poor the second time around.
It was proving to be a busy night for McGregor - who, thankfully for Rangers, signed a new long-term contract this summer - and he did well to block from Jiloam Hamad in the final minutes of the match and keep his side's hopes of progression alive for now.