Udinese continued Tottenham’s miserable run of form by inflicting a 2-0 defeat on the North London side, reduced to 10 men, in the opening match of UEFA Cup Group D.
Antonio Di Natale scored a first-half penalty after a howler by Spurs goalkeeper Heurelho Gomes (pictured) to put the second-placed Serie A side in the lead.
Jamie O’Hara collected two yellow cards in a minute for tackles on Alexis Sanchez in the second half to see red and leave manager Juande Ramos in further trouble.
Substitute Simone Pepe made sure late on when he finished a breakaway move after excellent work by the impressive Fabio Quagliarella.
Tottenham looked a side lacking confidence, exemplified when Didier Zokora failed to control a simple ball on the touchline and, at more cost, when O’Hara moved well away from goal when in a great position to shoot close in with goalkeeper Samir Handanovic stranded.
Under-fire coach Juande Ramos had omitted winger David Bentley, who had earlier criticised his team-mates, from the squad.
It was his replacement Aaron Lennon who caused most of the problems for the home defence, repeatedly scampering down the right but unable to supply a decisive final ball.
After a couple of hairy early moments Spurs looked settled into the match, building their play from a solid base, only for Brazilian Gomes to make a hash of controlling a simple ball and allowing Quagliarella to steal in.
As the Italy star looked to turn and shoot, Gomes manhandled him – and down the striker went.
There were yellow cards for Gomes, perhaps lucky to stay on the field, and Alexander Lukovic for complaining too vociferously before Udine captain Di Natale struck the spot-kick into the corner.
Spurs did have opportunities to equalise – Darren Bent directed a pair of weak headers at goal and O’Hara had that chance – but their haphazard gameplan went out of the window when the midfielder made two rash challenges on Chile international Sanchez 10 and 11 minutes after the break.
There were further yellow cards, including one for left-sided midfielder Bale, who should have centred at least one of three attacking free-kicks he wasted through shooting.
Di Natale almost scored s sensational second with an outrageous lob with his instep after bringing the ball down; Gomes hauled his massive frame backwards to claw it away from on the line.
Substitute Giovani dos Santos looked lively although, with his side a man down, he had little space to work with. Nevertheless, he presented a gilt-edged chance to Bent from the byline with five minutes left to play.
The striker headed powerfully this time under the crossbar from outside the six-yard box, only to see Handanovic tip the ball over.
A minute later the second-goal cushion was added by Pepe, who scored off the inside of the post following a superb breakaway move to leave Tottenham contemplating a fifth game without a win.
Dinamo Zagreb 3-2 NEC Nijmegen
Dinamo Zagreb came from behind with two late goals to beat NEC at home.
Dinamo took the lead after three minutes through Marijo Mandzukic, only to concede an own-goal equaliser 20 minutes later through Carlos.
Tim Withelmus Janssen gave the Dutch side the lead with 12 minutes left, but Bosko Balaban and Ivica Vrdoljak hit two goals inside three minutes to seal the victory for the Craotian hosts.
