Rangers suffered their first defeat in ten weeks tonight going under 1-0 to AZ Alkmaar in the Netherlands, a result that leaves the Ibrox men still requiring at least one point against Auxerre in two weeks time to ensure qualification for the next stage of the UEFA Cup.
A packed house of 8,400 in the tiny ground saw manager Alex McLeish make two changes from Sunday with Michael Ball and Bob Malcolm replacing Maurice Ross and Hamed Namouchi, alterations that meant a change to the compilation of midfield.
UEFA Cup Defeat For Gers In Alkmaar
A one minute silence was immaculately observed prior to kick off in memory of Prince Bernard of the Netherlands who died last night at the age of 93.
Dado Prso tested Henk Timmer in five minutes with a 20 yard shot that was comfortably held but the light blues were caught cold 60 seconds later when Danny Landzaat netted from a Martijn Meerdink pass.
This was the very start Rangers least wanted and it was almost 2-0 immediately afterwards when Barry Van Galen's 20 yard volley flashed inches wide.
Landzaat was creating problems for the gers defence - clean through in 19 minutes he saw his shot held by Stefan Klos.
Rangers threatened 4 minutes later, Marvin Andrews flick from a Michael Ball cross being just too high.
Peter Lovenkrands came close on the half hour with a 20 yard shot that grazed the crossbar and 6 minutes later the scores should have been level when Nacho Novo disposessed Tim De Cler only to see Timmer block his effort.
The pace and technique of AZ continued to present problems to Rangers all over the field however and Klos had to be alert just before the interval touching wide a De Kler effort from a Kenneth Perez pass.
Namouchi replaced Lovenkrands at half time but it was AZ who threatened to increase their lead in 54 minutes, a Perez shot from a Landzaat pass being held by Klos.
Two minutes later Novo tested Timmer from a Prso opening but Rangers were lacking the killer punch.
Van Galen almost caught out Klos with a clever header in 65 mins with the backtracking goalkeeper proving equal to the task.
Stephen Hughes replaced Bob Malcolm on 72 minutes as Rangers began to apply some pressure on the home goal - Jean Alain Boumsong's 25 yard drive two minutes later being held by Timmer.
Rangers had a stonewall penalty denied in 80 minutes when a Hughes cross was clearly handled by Van Galen but Israeli referee Alon Yefet indicated the ball had struck his chest, which it certainly had not.
60 seconds later a Hughes header from a Fernando Ricksen cross was headed off the line by substitute Olaf Lindenbergh.
Rangers had ran out of time and in all honesty the home side were worthy winners, celebrating their win with a lap of honour to the delight of the home fans.
After the match Alex McLeish expressed his disappointment at losing to the early goal, saying "I warned the players that AZ are a very good side but one or two of our lot didn't get started in time. We're still in a good position. We now need to put pressure on Auxerre and not sit back and look for a draw."
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)