On 6 December 2008, Anderson won the 2008 Golden Boy award. On 21 December 2008, Anderson played 88 minutes of the 2008 FIFA Club World Cup final against LDU Quito, which United won courtesy of a single Wayne Rooney goal to claim the world title. On 1 March 2009, Anderson came on in the 56th minute of the 2009 League Cup final against Tottenham Hotspur, replacing Danny Welbeck. He went on to score the winning penalty in the penalty shootout, winning his first League Cup medal. On 18 May, in the penultimate game of the season against Arsenal, United only needed one point to seal their third successive Premier League title and Anderson's second in two years at the club. Anderson was brought on for Wayne Rooney in the final minute, helping United lift the title at home to their fierce rivals.