Udinese Calcio 2–0 Tottenham Hotspur on 23 October 2008

Tottenham's problems continued to mount as they lost to Udinese in an eventful opening match in Uefa Cup Group D.

Udinese led when Spurs keeper Heurelho Gomes failed to clear a backpass then fouled Fabio Quagliarella - and Antonio Di Natale scored the resulting penalty.

Things got worse for Spurs when Jamie O'Hara was sent off after being booked twice inside a minute for rash fouls.

Darren Bent's header forced a fine save from Samir Handanovic but Simone Pepe's cool finish sealed victory for Udinese.

With his expensively assembled side bottom of the Premier League and speculation mounting over his future, Spurs boss Juande Ramos would have hoped for some respite in Europe, particularly in a competition he has won twice in the last three seasons with Sevilla.

But his build-up to this game was not helped by David Bentley's outspoken comments about Tottenham's poor start to the season and Ramos's response was to exclude the England winger from his matchday squad in Italy.

On the pitch it was the same old sorry story for Spurs as they again failed to translate some decent attacking play into a positive result.

Udinese poured forward purposefully in the early stages and the clever movement of their forwards caused Tottenham plenty of problems.

The presence of Ledley King in central defence, however, helped Spurs soak up most of the home side's pressure and meant Udinese's only effort on goal during that spell was an Andrea Coda header that drifted wide.

And Spurs were soon threatening themselves when Jermaine Jenas's cross found Bent at the far post, but his header was weak and straight at Handanovic.

It was a promising start for Ramos but all that good work was undone by Gomes's mistake, which came after 24 minutes when he attemped to control Benoit Assou-Ekotto's backpass but stumbled and allowed Quagliarella to nip in.

The Tottenham keeper attempted to salvage the ball but grappled with Quagliarella as he did so and, although the Italian striker's dive was exaggerated, it was a definite penalty which Di Natale despatched with ease.

Gomes has not been the root of Tottenham's difficulties this season but he continued to look nervous for the rest of the half, choosing to palm away Marco Motta's long-range shot when the ball could easily have fallen to a Udinese boot.

And by now Tottenham were creating far less, although Alan Hutton and O'Hara should both have done far better in front of goal when Handanovic failed to deal with a corner.

Udinese, in contrast, were growing in confidence and it took a fine save from Gomes to stop Quagliarella doubling their lead with a low shot after the break.

Spurs were still in the game at this point but their hopes were not helped by O'Hara's dismissal on 57 minutes.

German referee Felix Brych had just booked the England Under-21 star for his challenge on Alexis Sanchez when O'Hara repeated the trick to become the third Tottenham player to receive his marching orders in two matches.

Udinese's response was to up the ante and only two more superb Gomes saves, the first from close range to deny Maurizio Domizzi and the second to acrobatically keep out a Di Natale lob, stopped them from killing the game off.

Tottenham's 10 men were looking tired so it was something of a surprise when Bent almost snatched a late equaliser - his header being tipped over brilliantly by Handanovic.

But that was as good as it got for Ramos as, four minutes from the end, Pepe rounded off a quick breakaway move with a neat finish off the post that put the game beyond Spurs.