Possebon made his FA Cup debut on 13 February 2009, coming on as a 72nd-minute substitute for Cristiano Ronaldo in a Fifth Round fixture with Derby County. On 1 March 2009, Possebon won his second trophy in English football after he was part of the Manchester United squad that beat Tottenham Hotspur 4–1 on penalties after the 2009 League Cup final finished goalless. He had previously been part of the team that captured the 2008 FA Community Shield.