Born in Birmingham, Osbourne came through the Aston Villa academy and was handed his debut on 21st October 2006 against Fulham at Villa Park. In 2008, Osbourne moved to Leicester City on loan, only for Martin O’Neil to recall him due to injuries at Villa.

When Billy Davies took over at Nottingham Forest, Osbourne was the first player brought to the City Ground on a season long loan. He then went on to appear for Middlesbrough and Sheffield Wednesday before being released by Villa at the end of his contract.

Osbourne spent the 2011/12 campaign in Scotland, appearing over 30 times for Hibernian. In the summer of 2012, Blackpool handed Osbourne a two-year contract before he moved to Scunthorpe United and then Walsall.

On September 22nd 2017, newly promoted Forest Green Rovers signed the midfielder before he returned to Walsall last season.

Osbourne adds to the already experienced midfield at Liberty Way, with Nigel Julien, Michael Richens, Aman Verma and Jack Byrne all capable of being utilised as a central midfielder.