At the start of the 2008–09 season, Tottenham made its worst ever start to a campaign since 1912, losing six and drawing two of their opening eight Premier League matches. At that time, Assou-Ekotto's chances of first-team football were limited and he claimed that he wanted to leave England to go back to French football. However, Spurs manager Harry Redknapp decided to give Assou-Ekotto the chance to play in the team. He improved rapidly with regular matches and became first choice towards the end of the 2008–09 season. Having regained his fitness in the 2008–09 season, he became the North London club's first-choice left back due to a string of good performances under Redknapp. He started the 2009 League Cup final against Manchester United, where he played exceptionally well up against Cristiano Ronaldo. Even though Tottenham lost the match on penalties, Assou-Ekotto made left back his own position for the rest of the season as he made such a performance throughout the final. On 19 August 2009, he signed an extension to his contract keeping him at the club till 2013. Manager Redknapp praised Assou-Ekotto, saying, "I think he has been injured before but I have been very impressed with him this season as he has been in great form. He has looked an outstanding left back."