Rose began his career with Premier League giants Manchester United, spending five years at Old Trafford. Though he captained the Reserve side, he never played a senior game for the "Red Devils".
He impressed with his "sparkling displays" during his 22 Conference National appearances, and was signed on a month-to-month contract by manager Jim Smith in summer 2007. This came despite the Oxford Mail's report that he was "being chased by a number of Championship and League One sides – making a return to Oxford United seem highly unlikely". He made 19 appearances in 2007–08, before moving on to Newport County of the Conference South.
Newport County
He scored 10 goals in 2008–09, as Dean Holdsworth's side finished a disappointing 10th. He made 40 starts in 2009–10; Newport were crowned Conference South champions with a record 103 points, 28 points ahead of second-placed Dover Athletic. He started 50 matches in 2010–11, in which season Newport missed out on the Conference Premier play-offs by four places and nine points. He made 25 appearances in 2011–12 before being signed by Fleetwood Town for an undisclosed fee in January 2012. The move came despite interest from Football League clubs Aldershot Town and Crystal Palace. He had scored a total of 36 goals in 165 appearances in all competitions for Newport, including a hat-trick past Kettering Town on 18 October 2011.
On 13 June 2013, Rose joined Oxford United for the third time in his career. He signed a two-year-deal with an option of a third. On 1 February 2016 he left the club by mutual consent. He later signed for Northampton Town.
Northampton Town
On 1 February 2016, Rose completed a switch to Northampton Town. He scored his first goal for the club in a 1–0 win over Wycombe Wanderers on 20 February 2016.
On 3 June 2016, Rose joined Portsmouth. He scored his first goal for the club in a 5–1 win over Barnet on 24 September 2016. He was a key member of the team that won the League Two title in 2016–17. On 30 December 2017, in a match against Northampton Town, Rose broke his leg. The injury would see him sidelined for the remainder of the season, but he signed a one-year contract extension in March 2018. He made one further League appearance for the club in August.
Swindon Town
On 17 January 2019, Rose joined League Two club Swindon Town, signing a contract until the end of the 2018–19 season with the option of a further year. Rose signed a 1-year extension for the 2019–2020 season.
