Udinese add to Tottenham's troubles

Contrasting fortunes
The Premier League team did not lose an away game in the UEFA Cup last season en route to the Round of 16 where Heurelho Gomes, then of PSV Eindhoven, halted Tottenham's progress in a penalty shoot-out. However, it was Gomes's error at the Stadio Friuli, pulling down Udinese Calcio's Fabio Quagliarella, which led to Di Natale tucking away the opening goal from the penalty spot on 24 minutes. Substitute Simone Pepe added a late second four minutes from time.

Gomes guilty
Second in Serie A, Udinese tested Tottenham's ability to deal with set-pieces early on but gradually the visitors settled and Darren Bent registered their first effort on goal after 15 minutes. Samir Handanovič then made heavy weather of Aaron Lennon's cross-shot but no sooner had Spurs gained a foothold in the match, they became the architects of their own downfall when Gomes conceded a spot-kick after inadvertently letting Benoit Assou-Ekotto's back-pass run loose.

Pressure builds
Di Natale's successful conversion became the cue for a period of sustained pressure from the Italian side, Marco Motta forcing the Brazilian into a diving save to beat out his drive from distance. Six minutes after the restart, Gomes was called upon again to turn a shot from Italian international Quagliarella around the post.

Ten men
If Tottenham were already facing an uphill struggle, then their night worsened on 57 minutes when Jamie O'Hara collected his second caution in the space of 52 seconds. Gomes then expertly kept out Di Natale's deft lob but the real drama came in the final five minutes when Bent's header from point-blank range was somehow touched over by Handanovič and Udinese went straight up the other end to score a second as Pepe finished off Quagliarella's lay-off with the aid of a post.