He then joined Croydon Athletic before scoring the winning goal for Cray Wanderers in the Isthmian League Division One South play-off final.
He joined the coaching staff at Margate in 2013 and was appointed joint manager with Craig Holloway in April 2013 before losing his job eight months later.
A central midfielder, Osborn started his career as a trainee at Crystal Palace in January 1990 under the stewardship of Steve Coppell.
[2] He turned professional for the 1989–90 season when his performances for a newly-promoted Palace side secured their First Division survival with a 15th-place finish and saw him voted Young Player of the Year by the club's fans.
New boss Alan Smith led the "Eagles" to the First Division title in 1993–94, Osborn's last season at Selhurst Park.
They went on to lose 4–3 to Bolton Wanderers in the play-off final at Wembley; the game was necessary due to the Premier League's reduction in size only allowing one automatic promotion place.
[5] As a result of Reading's failure to secure promotion, Osborn decided to move away from Elm Park to gain Premier League experience.
Osborn scored six goals in 39 games in 1996–97, as Wolves finished third, four points behind Barnsley in the automatic promotion places; they went on to lose to his former club Crystal Palace at the play-off semi-finals.
Osborn started the 2006–07 campaign with Hereford United, a club Graham Turner had led to promotion back to the Football League after nine years in the Conference.
The "Ravens" finished the 2006–07 season as runners-up of the Isthmian League and beat Billericay Town in the play-off final to win promotion into the Conference South.
He was appointed player-manager of Bromley in January 2008, assisted by Bobby Bowry, but resigned three months later following a change in ownership, having led them to an eleventh-place finish in 2007–08.
He signed for league rivals Cray Wanderers in February 2009, appearing on the bench against Ashford Town and making his debut for the club in March against Walton & Hersham.