Career
His preferred position is winger. Born in Doncaster, Osborne made his league debut for Bradford City when he came on as substitute in the final 10 minutes of City"s 2–2 draw with Millwall in the final game of the 2006-2007 season. Osborne subsequently apologised for his misdemeanor and was reprimanded by the club and manager Stuart McCall, and remained at the club
McCall later said: "Leon’s not a bad lad but just a bit of a kid at times.
We all do silly things and he just needed to mature." He did not play for the first team during the 2007-2008 season, but was offered a new contract, and signed until the end of the year in May 2008. He earned a place on the bench for several games during the first few months of the 2008-2009 season but did not make an appearance, until his first senior start for an first round game at Milton Keynes Dons in November 2008.
He joined Southport on loan in August 2011. He signed for Harrogate Town in August 2012.
Outside of football Osborne was reported to have entered a relationship with famous Bradfordian Ashleigh Marsden.