Gary Osbourne had played in the Football League for Shrewsbury Town when he arrived on trial with Exeter City ahead of the 1989/90 season. He later helped Colchester United to return to the Football League after relegation to the Conference.

A former England under-16 international, he signed for Shrewsbury Town as a professional in 1988 and made four league appearances before his release from Gay Meadow in May 1989. Without a club at the start of the following season, he journeyed to Devon for a trial with the Grecians but was not offered a deal. 

Returning to Shropshire, he had brief stints with Telford and Stourbridge before signing for the recently-relegated Colchester United in March 1991 who were bidding to make an immediate return to the Football League. Having helped the Essex club to this objective, he was released at the end of the campaign and subsequently played for a variety of clubs in the West Midlands including Cradley Town, Bilston, Redditch United, Sutton Coldfield Town and Tamworth.