Grays Athletic, Dagenham & Redbridge, Chelmsford City (Loan), Ebbsfleet (Loan), Concord Rangers (Loan), Hayes & Yeading (Loan), Maidstone (Loan), Whitehawk (Loan), Margate, Whitehawk, Hemel Hempstead Town, East Thurrock United
The wide midfielder and forward re-joined Chelmsford City in May 2019 after leaving East Thurrock United.
Osborn, 25, started his career with Grays Athletic in 2009 before signing for Dagenham & Redbridge in 2010, where he stayed for 6 years.
During his time with the Daggers, Osborn went out on loan to Ebbsfleet, Concord Rangers, Hayes & Yeading, Maidstone and Whitehawk. He also spent time on loan with ourselves during the 2011/12 season, making 12 appearances.
Upon leaving Dagenham & Redbridge in June 2016, he signed for Margate as a free agent briefly before re-joining Whitehawk permanently 3 months later.
He signed for Hemel Hempstead Town in July 2017 and stayed with the Tudors for one-and-a-half seasons before leaving for National League South strugglers East Thurrock United in December 2018. He was, however, unable to prevent the Rocks from suffering relegation at the end of the 2018/19 season. Though he was a part of the East Thurrock squad that won last seasons BBC Essex Senior Cup, winning 3-1 against ourselves at Colchester United's JobServe Community Stadium; Osborn scored the 3rd goal to seal the victory for the Rocks.