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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.

Bjorn Vleminckx opened the scoring for Bruges just after the break against a Braga side who had defender Elderson sent off in the 16th minute for a trip on Vadis Odjidja but the Portuguese outfit equalised with a fine strike from Ewerton in the 65th.

English Championship side Birmingham City beat Maribor 1-0 but finished a point behind group winners Bruges and Braga who had already qualified.

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.

The draw for the round of 32 will be held on Friday.


Tottenham needed a win combined with a defeat for Rubin and had to make up a difference of five goals to qualify and, although it looked impossible to start with, it was on the cards at the break in the respective games.

"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."

Rubin fell behind to a Vierinha penalty in the 16th minute after their goalkeeper Sergei Ryzhikov was sent off for scything down Giorgos Georgiadis, while a second-string Tottenham side had opened up a three-goal half-time lead at Shamrock.

But Paraguay forward Nelson Haedo Valdez scored for Rubin three minutes after the break, volleying in from the penalty spot after Gokdeniz Karadeniz had cut the ball back.

South Africa midfielder Steven Pienaar, with his first goal for Spurs, Andros Townsend and Jermain Defoe struck in a 16-minute spell before half-time to keep the Londoners in the hunt.

Substitute Harry Kane then added the fourth in stoppage-time for Tottenham, who have fielded under-strength teams in all their group games.

Shamrock's de