Ipswich born Adrian Pennock made only one appearance for Norwich City ( a 4-1 defeat against Southampton on 17th February 1990) before moving onto Bournemouth in 1992 for £25,000. He had signed for the Canaries as Associate Schoolboy in November 1986 although he had been at Ipswich's school of excellence originally. Despite competition from Ipswich, Norwich signed him when Ipswich failed to make him an offer. Adrian progressed through the ranks at Carrow Road. He even had the obligatory "coming of age" loan period to Scandinavia (Molde Fotballklubb).

After 131 appearances for the South Coast club, Adrian suffered a career threatening injury. He managed to recover from this and then signed for Gillingham in October 1996. He has now made over 150 appearances for Gillingham (155 by the end of 2000/01)

Gillingham reached the Division Two play-offs in 1998/99 but lost on penalties to Manchester City At Wembley after a 2-2 draw. Adrian was one of the unlucky players to miss a penalty for Gillingham. At the end of January 2001, Adrian was linked with a move to Reading.

Adrian retired at the beginning of 2003, aged 31 following his 11th operation since damaging cruciate ligaments in his right knee at Bournemouth eight years previously. A chance to remain playing football in Kent materialised within days with both Dover (Dr Martens League) and Gravesend & Northfleet (Conference) expressing an interest in Pennock. Essex side Canvey Island (Rymans League) were also linked (The Non-League Paper). The conference side eventually won the battle for Pennock's services signing him and former Bristol Rovers striker Dwayne Plummer on Tuesday 21st January 2003. Pennock was also appointed to coach Gravesend's Under 19 side.

On 31st October 2003, Adrian received a treat when he was appointed assistant manager to replace Phil Handford who was leaving Gravesend.

In January 2005, Nationwide South club Welling United announced the appointment of Adrian Pennock and Phil Handford as the new managerial team at Park View Road. Pennock joins as first-team manager, whilst Handford, a former Welling favourite as a player who has also coached at Margate, will be Pennock's
assistant-manager.

Adrian left Welling at the end of the 2006/7 season to become an academy coach at Stoke City