Berlin - Premier League side Tottenham Hotspur slumped to a 1-0 defeat at Rubin Kazan on Thursday in a Group A Europa League match, leaving them third in the group.
Spurs went into the game with a three-point cushion over their opponents, but are now behind them on goal-difference, with both clubs having seven points.
PAOK Saloniki top the group with eight points after beating Shamrock Rovers 3-1 in Dublin.
In Kazan, Natcho scored the only goal of the game ten minutes after the restart with a well-taken free-kick.
Rubin dominated the match against Spurs, who travelled to Russia without their manager Harry Redknapp, who underwent heart surgery on Wednesday.
Spurs' Italian keeper Carlo Cudicini was in outstanding form and had it not been for his saves they would have lost by a much higher score.
In Group C PSV Eindhoven and Legia Warsaw advanced to the knock-out stage. Although the Dutch club were held to a 3-3 draw at home by Hapoel Tel Aviv, they advanced, as did Warsaw, who beat Bucharest 3-1.
Athletic Bilbao also advanced to the next round with a 1-0 victory at Red Bull Salzburg. The Spaniards are on 10 points and although they could sill be caught in Group F by Salzburg, they would be ahead on head-to-head.
French club PSG are second in the group on seven points after beating Slovan Bratislava 1-0.
Hanover 96 and Standard Liege took control of Group B with victories at Copenhagen and Vorskla Poltava respectively, leaving them on eight points - four more than third-placed Copenhagen.
Lazio played themselves back into contention in Group D with a 1-0 victory against Zurich to take them to five points, while FC Vaslui, who beat the already qualified Sporting Lisbon, 1-0, are also on five points.
Premier League club Stoke City won 2-1 at Maccabi Tel Aviv to move to 10 points in Group E, while Besiktas, who secured a 1-0 victory against Dynamo Kiev are on six points.
Europa League results on Thursday:
Rubin Kazan 1 Tottenham Hotspur 0
Shamrock Rovers 1 PAOK Salonika 3
Vorskla Poltava 1 Standard Liege 3
FC Copenhagen 1 Hanover 96 2
Legia Warsaw 3 Rapid Bucharest 1
PSV Eindhoven 3 Hapoel Tel Aviv 3
Vaslui 1 Sporting 0
Lazio 1 FC Zurich 0
Maccabi Tel Aviv 1 Stoke City 2
Besiktas 1 Dynamo Kiev 0
Salzburg 0 Athletic Bilbao 1
Paris St Germain 1 Slovan Bratislava 0
Metalist Kharkiv 3 Malmo 1
Austria Vienna 2 AZ Alkmaar 2
Braga 5 Maribor 1
Birmingham City 2 Club Bruges 2
Celtic 3 Stade Rennes 1
Atletico Madrid 4 Udinese 0
Schalke 04 0 AEK Larnaca 0
Steaua Bucharest 4 Maccabi Haifa 2
Twente Enschede 3 OB Odense 2
Fulham 4 Wisla Krakow 1
AEK Athens 1 Lokomotiv Moscow 3
Anderlecht 3 Sturm Graz 0