Born in Birmingham, West Midlands, Osbourne was given the squad number 27 after Martin O'Neill's arrival at Aston Villa. He made his Premier League debut on 21 October 2006, when he came on as a substitute in the 83rd minute for Steven Davis against Fulham at Villa Park. 28 December 2006 saw Osbourne sign a new three-and-a-half-year contract, keeping him at Villa Park until the summer of 2010. On 10 January 2008, Osbourne agreed to join Ian Holloway's Leicester Cityon loan, however just a few days later Villa manager Martin O'Neill was forced to cancel the proposed deal because of mounting injury concerns. He showed his talent with an impressive cameo for Villa in a 1–1 draw at Arsenal in March 2008. On 23 September 2008, Osbourne extended his contract with Aston Villa until 2011. He featured in a handful of cup matches for Villa in 2008–09. On 2 March 2009, he became the first player to move to Nottingham Forest under Billy Davies' reign, joining on loan until the end of the season. He made his debut against Preston North End on 3 March 2009. Osbourne made eight appearances for Forest in the Championship before returning to Aston Villa. Osbourne joined Gordon Strachan's Middlesbrough on 5 November 2009. The loan signing made his debut for Boro in a 1–0 defeat at the hands of Crystal Palace at Selhurst Park. Middlesbrough wanted to extend his loan spell, but Osbourne was recalled by Villa due to an injury crisis. In February 2010, Osbourne was expected to join Queens Park Rangers on loan, but the deal was not completed. Osbourne told the Birmingham Mail in July 2010 that he expected to remain with Aston Villa for the remaining year of his contract, in the hope that he could force his way back into the first team. Throughout his Villa career, Osbourne found his first team opportunities limited, making just 26 appearances between 2006 and 2011. During the 2009–10 season, he did not play a single minute of football for the club and only made one substitute appearance in the UEFA Europa League the following season. Osbourne was loaned out on 30 January 2011 to League One club Sheffield Wednesday, managed by Alan Irvine. After Irvine was sacked and replaced by Gary Megson, Osbourne was dropped out of the first team, with Megson preferring to bring in his own players. His loan deal was terminated early and he returned to Aston Villa on 5 April. Osbourne made a total of 11 appearances for The Owls. Osbourne was released by Aston Villa when his contract expired in May 2011.
Osbourne joined Leeds United on trial in July and he played for Leeds in friendlies against Rochdale and Sheffield Wednesday.But was unable to earn a permanent deal.
Hibernian
Osbourne signed with Hibernian, and he soon agreed a two-year contract with the Scottish Premier League club. Osbourne made his Hibernian début on 14 August 2011 in a 4–1 away loss at Kilmarnock, coming off the bench at half-time to replace Lewis Stevenson. On 24 September 2011, Osbourne scored with a deflected shot in a 3–3 home draw with Dundee United, but it was officially recorded as a Scott Robertson own goal. Osbourne scored one goal for Hibs in 35 appearances during the 2011–12 season.
Blackpool
signed Osbourne in July 2012 on a one-year contract, with an option for a second year. He left the club at the end of the 2013–14 season after his option was not taken up.
On 22 September 2017 Osbourne signed a contract until the end of the 2017–18 season for newly promoted League Two side Forest Green Rovers. He was released by Walsall at the end of the 2018–19 season.
Nuneaton Borough
In October 2019 he signed for Nuneaton Borough.
Personal life
Osbourne attended Kingsbury School and Sports College. His brother, Isaac, is a professional footballer who has played for Coventry City and Aberdeen. Growing up, he supported Arsenal. He named former Gunners captain Patrick Vieira as one of his footballing role models. In October 2009, Osbourne was arrested on suspicion of conspiracy to rob whilst training at Aston Villa's Bodymoor Heath Training Complex. No charges were ever brought against him. Osbourne says that the arrest was as a result of a Mercedes Benz which he had tried to sell on Auto Trader - which a group of men had attempted to purchase with counterfeit money. Despite nothing ever coming of the arrest, Osbourne considers it something that has had a negative effect on his footballing career. He described his move to the SPL was partly down to a need to "get away from it all".
