Goals from Antonio Di Natale and Simone Pepe condemned ten-man Tottenham Hotspur FC to defeat and ensured that the London club's early-season woes showed no signs of abating.
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.
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.
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.
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.