AZ Alkmaar 1 Rangers 0
UEFA Cup Group F: Rangers' unbeaten run came to an end in Alkmaar after an early goal from Denny Landzaat gave AZ victory in this UEFA Cup tie in the Netherlands.
The result was Rangers' first reverse in 17 games and they must now avoid defeat at home to Auxerre in their final Group F fixture to join the Dutch side in the knockout stages of the competition after Christmas.
Rangers were second-best on the night to AZ, who were the group's lowest seeds when the draw was made back in September.
A huge slice of the pre-match hype concerned Fernando Ricksen's return to the club which sold him for £3.6 million four years ago, but he made minimal impact.
Instead, it was Landzaat who caught the eye early on and the Dutch international netted in only the seventh minute.
Ricksen's rebirth as a central midfielder meant Zura Khizanishvili operated as a makeshift right-back and the Georgian struggled as AZ attacked relentlessly down the left.
The goal came from that side of the pitch. Tim de Cler found Martijn Meerdink with a low cross and his simple lay-off was perfect for the onrushing Landzaat to stroke past an exposed Stefan Klos.
The German was called on to deny Landzaat a second in the 20th minute after he was put through on goal by another series of swift passes from a side who are ahead of Ajax and Feyenoord in the Dutch top flight.
Klos' efforts were matched at the other end by AZ's Henk Timmer, who produced a fine stop nine minutes before the break to deny Nacho Novo, whose effort was weak after he managed to stay on his feet under challenge from Barry Opdam.
Even Jean-Alain Boumsong, usually his side's most accomplished defender, was finding life in the Alkmaarderhout Stadium difficult.
Hamed Namouchi replaced the ineffectual Peter Lovenkrands at the break, with the Dane seemingly having suffered a hamstring injury.
Although Rangers threw bodies forward in the second half they could make nothing of a flurry of free-kicks.
Ricksen was required to make a block on the edge of his own box to deny Barry van Galen, who had come thundering in to launch a drive. The veteran van Galen almost made it 2-0 after the hour mark when Klos came to collect a cross only for Ball to hook it away from him. Van Galen headed towards an empty net but Klos recovered his ground to catch.
AZ survived a strong shout for a penalty when a cross from Hughes hit van Galen's hand, but Israeli referee Alon Yefet rejected the appeal.
Hughes almost conjured up an equaliser by diverting an Andrews header past Timmer with his head but substitute Olaf Lindenbergh was on the line to head clear.
AZ ALKMAAR:Timmer, Kromkamp, Mathijsen, Opdam, De Cler, Buskermolen (Lindenbergh 19), Landzaat, Meerdink, Huysegems (Nelisse 88), Van Galen (Ramzi 83), Perez. Subs Not Used: Zwarthoed, Fortes Rodriquez, Jaliens, Sektioui. Booked: De Cler. Goal: Landzaat 7.
RANGERS:Klos, Khizanishvili, Ball, Boumsong, Andrews, Malcolm (Hughes 72), Alex Rae, Ricksen, Prso, Lovenkrands (Namouchi 45), Novo. Subs Not Used: Graeme Smith, Hutton, Mladenovic, Steven Smith, Davidson. Booked: Ball, Malcolm.
Referee:Alon Yefet (Israel).