Born in Leytonstone, east London, Kilbey was originally signed to Millwall where he made his first team debut against Swansea City in September 2007 at the age of 16 in the Football League Trophy in a defensive midfield role.
[2] In October 2007, Kilbey signed a contract with Premier League team Portsmouth moving for an undisclosed fee.
[3] During his first season on the south coast he established himself in the academy side with a strong pairing with fellow midfielder Marlon Pack.
This saw Kilbey put in some classy performances[citation needed] including scoring a hat-trick against West Bromwich Albion on 6 April 2009.
On 24 March 2011, Kilbey was loaned again, this time to League Two club Lincoln City, until the end of the season.