Rubin Kazan 1-0 Tottenham: Natcho free kick ends Spurs’ unbeaten run as Redknapp’s side drop from top spot

Tottenham Hotspur fell to a disappointing 1-0 defeat in Russia at the hands of Rubin Kazan thanks to Bibras Natcho’s second-half free kick.

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Rubin were deserved winners and could have had more if not for the sterling work of goalkeeper Carlo Cudicini, with his counterpart Sergei Ryzhikov in the Rubin goal completely untested.

The result sees PAOK, who beat Shamrock Rovers in Group A’s other fixture, climb to top spot.

With Harry Redknapp still in hospital recovering from heart surgery, Kevin Bond took charge of a Spurs side that retained just one player from their weekend victory over Queens Park Rangers. Sebastien Bassong kept his place at centre-back and was joined by William Gallas, who made his first start after returning from injury.

They were flanked by youngsters Ryan Fredericks and Andros Townsend, with Cudicini preferred to Heurelho Gomes in goal. Jake Livermore and Tom Carroll anchored the midfield with Iago Falque and Steven Pienaar in the wide positions supporting Jermain Defoe and Roman Pavlyuchenko.

Notable Tottenham tormentor Obafemi Martins was preferred to Nelson Valdez in attack for the home side, with Alan Kasaev and Gokdeniz Karadeniz supporting the lone striker.

Rubin had the better of the first half, regularly working Cudicini despite starting the game slowly. They will claim with some justification, however, that they could have had a penalty during that otherwise uneventful spell when Gallas blocked a cross with his arm.

Spurs looked comfortable during the early stages, holding possession high up the field but struggling to create space in the final third. Defoe and Pienaar were the most involved when Tottenham attacked, but they found themselves consistently crowded out by Rubin’s organised pressing.

As the home side settled, the tide began to turn. Kasaev had their first chance, volleying over the bar after skilfully controlling Karadeniz’s cross, and the two wide men would continue to cause Spurs real problems.

Cudicini was called into action three times in quick succession soon after that first effort, with Christian Noboa the first man denied when his powerful effort was palmed wide of the post.

Salvatore Bocchetti could not quite force home the resulting corner after the ball was allowed to drop around the six-yard box before Cudicini proved himself equal to Natcho’s superb curling effort from 25 yards.

Aleksandr Ryazantsev forced another good stop from Cudicini, although he might have been better served by picking out Martins across goal, as Rubin continued to press. The excellent Kasaev created the best chance of the half when his inch-perfect cross evaded Gallas only for Martins to fail to make good contact with his header.

Spurs finally made their way into the Rubin penalty area towards the end of the half, but Defoe’s good work went unrewarded when his low ball across the six-yard box evaded Pavlyuchenko.

Ten minutes after the break and Rubin had deservedly broken the deadlock. Bassong’s error and foul on the edge of the box was severely punished as Natcho, Rubin’s top scorer this season despite his deep midfield position, clipped a perfectly placed free kick over the wall and beyond a stranded Cudicini.

Natcho almost turned provider after that, slipping a through ball into Ryazantsev with a static Spurs defence left appealing for offside as the Russia international broke through, but Cudicini parried the shot away.

With Rubin leading, the responsibility to press and dictate the flow of the game fell to Spurs but the inexperience of their midfield started to tell as Defoe and Pavlyuchenko showed glimpses of combination play but lacked support.

Ryazantsev continued to create space with some well-timed breaks from midfield, shaving the crossbar with one 25-yard effort after Spurs had suffered a blow when Gallas went down with injury.

Dean Parrett replaced the Frenchman while Harry Kane was also introduced, but it was Rubin who continued to create chances on the counter through the pace of Karadeniz. The Turkish winger’s header was well saved by the feet of Cudicini as Spurs’ backup shot-stopper continued to stake his claim for a more regular place in the side, later denying substitute Nelson Valdez.

Rubin's lead remained slim until the final whistle but Spurs could not find a way through the Russians' mean defence, and will now find themselves in a tricky battle with their opponents, as well as PAOK, for a place in the next stage of the competition.