Bale signed a new 4-year deal with the club in August 2008.^[43] After some mediocre performances, Bale was dropped in favour ofBenoît Assou-Ekotto and the latter remained first-choice for most of the season.^[44]

2009–10 season

In June 2009, Bale underwent surgery for a knee injury, ruling him out for over 2 months. He missed pre-season matches and it was projected that he would miss the first few weeks of the 2009–10 season.^[45] On 26 September, he made his comeback as an 85th minute substitute in Tottenham's 5–0 thrashing of Burnley. This was Bale's first ever involvement in a Premier League win, after playing a record 24 league matches for Spurs without being on the winning side.^[46][47][48] However, he endured a frustrating time on the bench as Benoît Assou-Ekotto was in good form. When Assou-Ekotto was sidelined with an injury, manager Harry Redknapp decided to give Bale a chance and he impressed in Spurs' FA Cup third-round 4–0 win over Peterborough.^[49] He finally tasted victory for the first time as a starter in a league game in the 2–0 win over London rivals Fulham on 26 January 2010.^[50]

Bale's good form continued and he was named Player of the Round after helping Spurs to a 3–1 win in the sixth round replay of the FA Cup against Fulham.^[51] In April 2010, Bale scored the winning goal in a 2–1 North London derby win against Arsenal, tapping past Manuel Almunia after a pass from Jermain Defoe.^[52] Three days later, Bale scored Tottenham's winning goal with his weaker right foot in a 2–1 victory over league leaders and eventual champions Chelsea and was named Man of the Match.^[53] He was named Barclays Player of the Month for April 2010.^[54] He signed a new four-year contract at White Hart Lane on 7 May 2010 as a reward for helping the club reach the Champions League qualification place.