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.