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Birmingham and Celtic fail to reach last 32

Rubin Kazan, down to 10 men after 13 minutes, held on for a 1-1 draw at PAOK Salonika to qualify at the expense of last season's Champions League quarter-finalists Tottenham Hotspur.

The under-strength English Premier League side, with only three outfield players on the bench, won 4-0 at Shamrock Rovers but finished third in Group A, one point behind the Russians.

Udinese's Antonio Di Natale volleyed an equaliser in first half stoppage-time to give the Italians the point they needed at home to Celtic who had taken the lead through Gary Hooper. The 1-1 draw left Udinese second in Group I behind Atletico Madrid.

Bruges also went through with a 1-1 home draw versus last year's Europa League finalists Braga, who played most of the Group H match with 10 men, as did Dutch league leaders Alkmaar by the same scoreline against Metalist Kharkiv in Group G.

Alkmaar's Adam Maher equalised seconds after Metalist went ahead late in the first half through Marko Devic and the point kept the Dutch side in second place just above Austria Vienna, who beat visitors Malmo 2-0, on goal difference.

"At half-time we knew that the other team [Rubin] were losing and thought we had a real chance," Spurs manager Harry Redknapp told ITV4. "We knew they had gone down to 10 men."

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