Career
Osborne plays principally at centre-back, though he is also a capable right-back. Early years
He started his career at South Ruislip Rangers, playing under the management of Keith Robins for a number of years. Despite starting his first few games as a striker/midfielder, he was soon gelled into a centre half, where he held together the South Ruislip back line.
Brentford
Osborne joined League One side Brentford in the summer of 2004.
He quickly made an impression in the club"s youth and reserve teams and received his first call into the senior squad for a Football League Trophy first round match versus Milton Keynes Dons on 28 September 2004. Awarded the number 38 shirt, he remained on the bench for the 3–0 defeat.
Osborne was an unused substitute on two further occasions before making his Brentford debut against Hull in the final game of the 2004/05 season, starting the match and playing the full 90 minutes. He found appearances hard to come by the following season, making only three, though he started and played the full ninety minutes in each match.
He spent the final two months of the season on loan at Conference South side Hayes.
After Martin Allen left as manager and his squad was broken up, Osborne became a first team regular under Leroy Rosenior (and later Scott Fitzgerald) during the 2006/07 season, at the end of which Brentford were relegated to League Two. In the 2007-2008 season, in the absence of Matt Heywood and Kevin O"Connor, Osborne captained the team on several occasions. He had a one-month loan spell with Oxford United in September 2008.
On 10 October 2008, Osborne transferred to Eastbourne Borough for a one-month loan lasting until 6 November 2008.
He played three games and scored a goal against Barrow during a league game. He returned from his loan spells to play a key role in Brentford"s promotion from League Two.
In the 2009/10 season, his appearances were limited until March, when an injury crisis gave him an extended run of games in the team His good form resulted in a new contract at the end of the campaign.
In May 2012, Osborne was released after turning down a new deal earlier in the season.
Millwall
On 13 July 2012 Osborne agreed a free transfer to Kenny Jackett"s Millwall after sealing a 2-year deal. Brentford
League Two: 2008-2009.