Rangers slipped to second place in Uefa Cup Group F after a narrow defeat to an impressive AZ Alkmaar side in Holland.
The home team went ahead after seven minutes when a flowing one-touch move ripped open Rangers and allowed Danny Landzaat to fire past Stefan Klos.
Nacho Novo wasted Rangers' best chance - shooting straight at the home keeper 10 minutes before the interval.
And Stephen Hughes saw a header cleared off the goal-line nine minutes from time as Rangers finished strongly.
Rangers now go into their final group match with Auxerre at Ibrox on 15 December knowing a point will secure progress to the last 32 in the competition.
The home side came flying out of the traps and their crisp passing game had Rangers stretched right from the start.
Rangers right-back Zura Khizanishvili was given a torrid time as AZ mounted several promising attacks down the left flank.
Rangers replied with a sixth-minute drive from distance from Dado Prso, which goalkeeper Henk Timmer got behind.
However, the Dutch team were ahead a minute later following a slick move.
Landzaat scored by beating the exposed Stefan Klos when the Rangers defence was opened up by Martin Meerdink's simple lay-off after he had been located in the box by Tim de Cler.
Meerdink then fired a curling effort from outside the box just wide.
A Prso drive was blocked in the box by Landzaat and Peter Lovenkrands shot wide from 25 yards as Rangers rallied briefly.
Klos then saved his side with a superb block from Landzaat after he had been sent clear by more impressive build-up work from AZ.
Rangers threatened when Marvin Andrews flicked out a leg to meet a Michael Ball delivery but the defender could only send the ball over the bar.
A great chance came Nacho Novo's way in the 36th minute when Barry Opdam miscontrolled to allow the Spaniard to race goalwards.
Rangers were beaten by an impressive side
Opdam clipped him trying to recover but Novo stayed on his feet only to shoot tamely at Timmer.
As an entertaining first half drew to a close, Klos made a fine save at his near post to deny de Cler.
Klos was able to gather a low drive from Perez early in the second period as AZ continued to move the ball around with menace.
Rangers were clumsy in comparison but the strength of Prso was troubling the home side, who looked vulnerable in the air.
A mix-up between Ball and Klos saw the Rangers defender's desperate clearance go straight to Van Galen but Klos was able to race back and catch the midfielder's looping header from 22 yards.
As the game wore on, AZ lost some of their earlier zip and Rangers were winning more tackles in the midfield area.
Rangers came close to an equaliser in the 81st minute when substitute Hughes helped on Andrew's downward header from a corner but an AZ player was on the goal-line to nod clear.
But Alex McLeish's men could not find away through against the side that sit second in the Dutch Eredivisie and the SPL leaders' run of 16 games unbeaten came to an end.
AZ Alkmaar: Timmer, Kromkamp, Mathijsen, Opdam, De Cler, Buskermolen, Landzaat, Meerdink, Huysegems, Van Galen, Perez. Subs: Zwarthoed, Fortes Rodriquez, Jaliens, Ramzi, Lindenbergh, Nelisse, Sektioui.
Rangers: Klos, Khizanishvili, Ball, Boumsong, Andrews, Malcolm, Alex Rae, Ricksen, Prso, Lovenkrands, Novo. Subs: Graeme Smith, Namouchi, Hughes, Hutton, Mladenovic, Steven Smith, Davidson.
Referee: Alon Yefet (Israel)