A superb display by Tottenham keeper Carlo Cudicini could not stop Spurs slipping to defeat against Rubin Kazan in a one-sided Europa League encounter.
Cudicini denied Christian Noboa, Bebras Natcho and Aleksandr Ryazantsev before the break as Rubin poured forward.
But he could not stop Natcho's curling free-kick, conceded after Sebastien Bassong was caught in possession.
Spurs, who were without boss Harry Redknapp after his heart surgery, failed to create a clear-cut chance.
Redknapp is expected to be back in the dugout when Spurs play Fulham at Craven Cottage on Sunday but it was left to his assistant Kevin Bond to take a young team to Russia looking for the win that would put them through to the last 32.
In truth, Tottenham never really looked like taking all three points and this defeat means they face a battle to reach the knockout stages -with their next home game against PAOK Salonika on 30 November likely to prove decisive.
After a slow start, it was the home side who began to up the ante. Gokdeniz Karadeniz caused Spurs problems with his raids down the right and Alan Kasaev fired narrowly over from one of his pull-backs.
Another Karadeniz cross led to Cudicini's first save of the night, with the Spurs keeper making up for a weak punch by brilliantly pushing away Christian Noboa's snap-shot.
Two more top-class stops followed quickly afterwards, first from Natcho's rasping shot which was heading into the top corner, and then to deny Ryazantsev at his near post.
At the other end, Jermain Defoe and Roman Pavlyuchenko were struggling to get into the game and the one-way traffic continued when former Newcastle and Birmingham striker Obafemi Martins headed wide from Kasaev's clever cross.
Tottenham did have a sniff of goal when Defoe's drilled cross just eluded his strike partner at the far post but their best effort came early in the second half when Ryan Fredericks cut in from the right before firing into the side netting.
Rubin continued to come forward and got their reward when Bassong's poor control led to him fouling Ryazantsev and conceding a free-kick right on the edge of the area.
This time Cudicini was left helpless when Natcho stepped up to expertly curl the ball into the top corner.
That was the cue for further pressure from the Russian side and it took further Cudicini saves to keep the score down.
He pushed away Ryazantsev's shot and kept out a Karadeniz header before instinctively stopping Nelson Valdez's rasping effort.
Tottenham, who lost William Gallas to injury before the end, struggled to find any sort of response and did not register a single shot on target.
Live Text Commentary
Full Time The match has reached full-time.90:00 +3:31
Andros Townsend sends in a cross, clearance made by Gonzalez Cesar Navas.90:00 +2:18
Alexei Eremenko takes a shot. Save by Carlo Cudicini.90:00 +1:58
Nelson Haedo Valdez takes a shot. Save by Carlo Cudicini.90:00 +0:37 Booking
Booking Alexei Eremenko receives a yellow card for unsporting behaviour.87:20 Substitution
Substitution Alexei Eremenko comes on in place of Alexander Ryazantsev.87:20
Bebras Natcho decides to take the corner short.87:20 Booking
Booking Alexander Ryazantsev booked for unsporting behaviour.87:10
Steven Pienaar produces a cross, save by Sergei Ryzhikov.86:42
Unfair challenge on Steven Pienaar by Alexander Ryazantsev results in a free kick. Ryan Fredericks takes the direct free kick.84:27
Dean Parrett gives away a free kick for an unfair challenge on Alexander Ryazantsev. Free kick taken by Alexander Ryazantsev.82:42 Substitution
Substitution Cristian Ansaldi is brought on as a substitute for Alan Kasaev.80:57
The ball is sent over by Gokdeniz Karadeniz, Nelson Haedo Valdez takes a shot. Carlo Cudicini makes a save. Short corner taken by Bebras Natcho from the left by-line, comfortable save by Carlo Cudicini.79:26
Gokdeniz Karadeniz takes a shot. Carlo Cudicini makes a save.77:45
Andros Townsend challenges Bebras Natcho unfairly and gives away a free kick. Free kick taken by Bebras Natcho.75:54
Steven Pienaar fouled by Nelson Haedo Valdez, the ref awards a free kick. Free kick crossed right-footed by Harry Kane from left wing.74:43 Substitution
Substitution Roman Pavlyuchenko leaves the field to be replaced by Harry Kane.74:26
Effort on goal by Alexander Ryazantsev from outside the area goes harmlessly over the bar.73:33
Centre by Gokdeniz Karadeniz, Sebastien Bassong gets a block in.72:51
Bebras Natcho gives away a free kick for an unfair challenge on Steven Pienaar. Steven Pienaar takes the free kick.
Substitution Dean Parrett joins the action as a substitute, replacing William Gallas.70:37
Cristian Noboa gives away a free kick for an unfair challenge on Sebastien Bassong. Free kick taken by Carlo Cudicini.66:00
Sebastien Bassong gives away a free kick for an unfair challenge on Gonzalez Cesar Navas. Direct free kick taken by Gonzalez Cesar Navas.65:50
The offside flag is raised against Nelson Haedo Valdez. Free kick taken by Carlo Cudicini.64:25 Substitution
Substitution (Rubin Kazan) makes a substitution, with Nelson Haedo Valdez coming on for Obafemi Martins.63:59
Obafemi Martins takes a shot from just inside the penalty box which clears the bar.62:33
William Gallas concedes a free kick for a foul on Gokdeniz Karadeniz. The ball is crossed by Bebras Natcho, Effort on goal by Salvatore Bocchetti from deep inside the area goes harmlessly over the bar.60:25
Alexander Ryazantsev takes a shot. Save made by Carlo Cudicini. Short corner worked by Bebras Natcho.58:38
Free kick awarded for an unfair challenge on Thomas Carroll by Cristian Noboa. Direct free kick taken by Ryan Fredericks.56:27
The ball is swung over by Gokdeniz Karadeniz, Sebastien Bassong manages to make a clearance.54:50 Goal scored
Goal! - Bebras Natcho - R Kazan 1 - 0 Tottenham Bebras Natcho grabs a goal direct from the free kick from just outside the box to the bottom left corner of the goal. Rubin Kazan 1-0 Tottenham.53:50 Booking
Booking Jermain Defoe goes into the book.53:45 Booking
Booking Sebastien Bassong receives a caution.53:34
Sebastien Bassong gives away a free kick for an unfair challenge on Alexander Ryazantsev.52:58
Foul by Bebras Natcho on Jermain Defoe, free kick awarded. Jermain Defoe takes the direct free kick.51:36
Jake Livermore concedes a free kick for a foul on Cristian Noboa. Alan Kasaev takes the free kick.51:22
The assistant referee signals for offside against Roman Pavlyuchenko. Indirect free kick taken by Sergei Ryzhikov.49:29
Foul by Alan Kasaev on Steven Pienaar, free kick awarded. Jake Livermore takes the free kick.47:03
Corner from right by-line taken by Bebras Natcho.45:48
Free kick awarded for an unfair challenge on Alan Kasaev by Steven Pienaar. Cristian Noboa has an effort direct from the free kick, Sebastien Bassong gets a block in.45:01
The referee gets the second half started.45:00 +0:56 Half time
Half Time The first half comes to an end.43:07
Unfair challenge on Andros Townsend by Gokdeniz Karadeniz results in a free kick. Free kick taken by Andros Townsend.34:56
Alexander Ryazantsev delivers the ball, Carlo Cudicini makes a save.34:30
Bebras Natcho takes a short corner.34:08
The ball is sent over by Alan Kasaev, William Gallas gets a block in.32:44
Alexander Ryazantsev takes a shot. Carlo Cudicini makes a save. Inswinging corner taken by Bebras Natcho.31:48
The ball is sent over by Gokdeniz Karadeniz, save by Carlo Cudicini.28:05
Bebras Natcho takes a shot. Save made by Carlo Cudicini. Outswinging corner taken from the right by-line by Gokdeniz Karadeniz.26:43
Obafemi Martins takes a shot. Carlo Cudicini makes a save.25:20
The ball is delivered by Gokdeniz Karadeniz, Effort from inside the area by Cristian Noboa misses to the left of the target.22:20
A cross is delivered by Gokdeniz Karadeniz, Effort from deep inside the area by Alan Kasaev clears the bar.20:58
The referee blows for offside against Roman Pavlyuchenko. Sergei Ryzhikov takes the free kick.19:41
Free kick awarded for an unfair challenge on Jake Livermore by Alexander Ryazantsev. Jake Livermore takes the free kick.17:46
Effort from the edge of the area by Roman Pavlyuchenko goes wide of the right-hand upright.16:09
Unfair challenge on Jake Livermore by Bebras Natcho results in a free kick. Andros Townsend takes the free kick. Gokdeniz Karadeniz concedes a free kick for a foul on Ryan Fredericks. Ryan Fredericks takes the free kick.14:43
Unfair challenge on Iago Falque by Salvatore Bocchetti results in a free kick. Ryan Fredericks restarts play with the free kick.12:31
Jermain Defoe takes a shot. Gonzalez Cesar Navas gets a block in.6:42
Gokdeniz Karadeniz takes a shot. Blocked by Sebastien Bassong.6:07
Sebastien Bassong concedes a free kick for a foul on Alan Kasaev. Salvatore Bocchetti restarts play with the free kick.0:00
The game gets underway.
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