Tottenham's second string were no match for Rubin Kazan in Russia on Thursday evening, Carlo Cudicini's heroics keeping the home side to a 1-0 victory.
A curling free-kick from Bebras Natcho proved decisive but Rubin would have scored many more times had Cudicini not denied Christian Noboa, Natcho and Aleksandr Ryazantsev with fine stops.
Gokdeniz Karadeniz caused a lot of problems for Spurs on the wing, his early pull-back blazed over by Alan Kasaev, before the wideman set up Noboa.
Cudicini, however, was equal to the snap-shot, and further brilliant efforts from Natcho and Ryazantsev - the first of which was heading for the top corner.
Obafemi Martins headed wide from a cross by Kasaev as Tottenham failed to get into the game - they failed to muster a clearcut shot in the entire game.
The decisive moment came after Bassong's poor control led to him conceding a free-kick right on the edge of the area, and Natcho stepped up to brilliantly curl the free-kick home.
It was a deserved win.