Career
Brentford
Lennie started his career as a junior at Brentford and received his maiden call into the first team squad for a Football League Trophy first round match versus Barnet on 14 October 2003. Lennie was an unused substitute on another four occasions during the 2003/04 season. Lennie made his professional debut in the Football League Trophy first round on 28 September 2004 against Milton Keynes Dons.
With the game already lost at 3–0, Lennie came on as a half-time substitute for Alan Julian.
He was called into the first team squad on another six occasions during the 2004/05 season, but did not play. Lennie was released during the summer of 2005.
Non-league football
After his release from Brentford, Lennie dropped into Non-League football. He played for AFC Wimbledon, Harrow Borough, Molesey, Chalfont Street Peter, Carshalton Athletic (two spells), Chertsey Town, (two spells), Skelmersdale United, Hayes & Yeading United, Salford City, Dorking Wanderers, Bedfont, Chester and Wingate & Finchley.
He also had a loan spell with Maidenhead United.