Tošić received his first taste of first team football on 20 January 2009, when he was named on the bench for United's League Cup semi-final second leg at home to Derby County. He made his debut in an FA Cup Fourth round match against Tottenham Hotspur on 24 January 2009, when he came on as a 72nd-minute substitute for Cristiano Ronaldo. Tošić's league debut came three days later, on 27 January 2009, when he came on as a 77th-minute substitute for his friend Dimitar Berbatov in United's 5–0 win over West Bromwich Albion. Although he did not make many first team appearances in his first season at Manchester United, Tošić became a regular in the club's reserve team, helping the team to a second-place finish in the Premier Reserve League before scoring the winning goal in the final of the 2009 Manchester Senior Cup against Bolton Wanderers at the Reebok Stadium.