Career
After beginning his career at youth level for Watford, Osman signed for Maidenhead United. With interest from other clubs, Osman then moved to the then Scottish Premier League club Gretna. Having failed a medical with fellow SPL side Kilmarnock, Osman returned to England and signed for Northampton Town.
After a successful three years, he then moved to Greek Superleague side Kerkyra.
However he soon returned to England and Crewe Alexandra. He was released by Crewe in 2014 and signed for Scottish Premiership side Partick Thistle in July 2014.
Osman began his career at Maidenhead United. After drawing interest from Crewe Alexandra, Osman moved to Gretna in the summer of 2007, signing a 12-month contract with the then SPL side, scoring once against Motherwell.
He became a free agent after the publicised troubles at Gretna, attracting interest from a number of clubs, Leeds United, Ipswich Town and Brighton all reported to be keen on him as well as various teams from Scotland.
In June 2008, Osman signed for then English League One side Northampton Town after failing a medical with Scottish Premier League side Kilmarnock. After two years, making over sixty appearances, Osman signed a week-to-week deal allowing him to look at other clubs. On 22 September 2010, Osman netted the winning penalty kick at Anfield, as Northampton knocked Liverpool team out of the League Cup.
In May 2011, along with seven other players, he was told his contract would not be renewed by the club
Osman went on trial at Greek Superleague side PAE Kerkyra in July 2011 and signed a two-and-a-half year contract in August 2011. On 25 July 2012, Osman joined newly promoted Football League One side Crewe Alexandra on a free transfer, signing a two-year contract.
After being released by Crewe in 2014, Osman went on trial at Scottish Premiership side Partick Thistle. He was signed by the Glasgow club on 23 July 2014.
On 15 May 2015, Osman signed a new one-year contract with Partick Thistle, keeping him at the club until the end of the 2015-2016 season.
Osman was made captain of Thistle at the beginning of the 2015-2016 season. With Crewe Alexandra.