Udinese 2 Tottenham 0:Embattled Spurs boss Juande Ramos has seen another of his players dismissed on the way to defeat, this time at the hands of Udinese in their opening Uefa Cup Group D clash.
Bottom of the Premier League with just two points from eight games, Spurs were hoping to pick themselves up from last weekend's defeat to Stoke in which they had both Michael Dawson and Gareth Bale sent off.
Instead, they conceded a 24th minute penalty that Antonio Di Natale converted, saw Jamie O'Hara dismissed for a second yellow card and were stung by a late second goal from Pepe when pressing on in search of an equaliser.
Club captain Ledley King returned to centre back for Spurs but O'Hara was preferred to Luka Modric who was introduced at halftime, while David Bentley was left out of the squad altogether and replaced by Benoit Assou-Ekotto.
The result leaves Spurs in familiar territory at the bottom of Group D.
Elsewhere, Aston Villa's Uefa Cup Group F rivals Hamburgbegan their bid to reach the knock-out stages with a 2-1 victory over Zilinain Slovakia.
Croatian forward Mladen Petric, whose goal for his country at Wembley last year ended England's hopes of qualifying for Euro 2008, got the first goal after 15 minutes for Hamburg.
Ivica Olic added a second before half-time as Hamburg secured an important win despite substitute Emil Rilke's second-half strike for Zilina.
CSKA Moscowand Schalkewere also early winners on the first matchday of this season's group stage.
Two goals in three first-half minutes from 18-year-old midfielder Alan Dzagoev paved the way for CSKA to post a 3-0 victory over Spanish side Deportivo La Corunain Group H, with Vagner Love completing the scoring just after the hour mark.
German side Schalke began Group A - which also contains Manchester City - with a 3-1 triumph over Paris St Germain.
They won thanks to an own goal by PSG defender Larrys Mabiala, plus goals from Kevin Kuranyi and Halil Altintop.
Clement Chantome hit a late consolation for the visitors, who were without former Chelsea midfielder Claude Makelele.