Osman started his career at Hampton & Richmond Borough before he moved on to play at youth level for Watford, before signing for Maidenhead United. After leaving the Magpies, Osman then signed for Gretnain the summer of 2007, signing a 12-month contract with the Anvils, scoring one goal versus Motherwell. Osman was then a free agent after the Anvils entered administration and he attracted interest from a number of clubs, with Leeds United, Ipswich Town and Brighton all reported to be keen on him, as well as various clubs from Scotland. In June 2008, Osman signed for Northampton Town after he failed a medical with Kilmarnock. On 22 September 2010, Osman netted the winning penalty-kick at Anfield Stadium, as the Cobblers knocked Liverpool out of the League Cup. In May 2011, along with seven other players, Osman was informed that his contract would not be renewed by the club. In July 2011, Osman then went on trial at Greek Superleague club Kerkyra and signed a -year contract in August 2011. On 25 July 2012, Osman then joined Crewe Alexandra on a two-year contract. After being released by the Railwaymen in 2014, Osman went on trial with Partick Thistle, before signing for the Harry Wraggs on 23 July 2014. Osman scored his first goal for the Firhill club on 13 September 2014, in a 3–1 win versus Inverness Caledonian Thistle, heading in from a corner to give his club a 2–1 lead. On 15 May 2015, Osman signed a new one-year contract with the Harry Wraggs, keeping him at the club until the end of the 2015-16 season. Osman was then appointed club captainat the beginning of the 2015–16 season. Osman was then sent-off in Thistle's 2–1 win versus St Johnstone. Thistle were relegated via the play-offs at the end of the 2017-18 season. Following the club's relegation, Osman was one of many players released by Thistle. On 17 August 2018, Osman returned to the Lamia. On [2 January">PAS Lamia 1964">Lamia. On [2 January 2019, after being released by Lamia during November 2018, Osman signed for Scottish Championship club Falkirk on 2 January 2019 until the end of the 2018-19 season. On 4 October 2019, after training with Dumfries club Queen of the South for a few weeks, Osman signed a short-term contract until 11 January 2020 and debuted against his former club Partick Thistle, as a second-half substitute. On 10 January 2020, Osman extended his contract with Queens until 31 May 2020.
