After a long professional career, chiefly in the colours of Leyton Orient and Portsmouth, Adrian Whitbread appeared for Exeter City on loan in 2003 towards the end of his playing days. He later worked alongside Martin Allen at a host of clubs  as well as coaching in Puerto Rico, Antigua and Bahrain.

Adrian became a professional with Leyton Orient in and, at twenty-one, captained a promotion-winning side. After 125 league appearances he joined Swindon Town in July 1993 for £500,000. The following year Adrian moved to West Ham United in part-exchange with Joey Beauchamp in August 1994 and, after just ten league appearances, was loaned to Portsmouth which led to a permanent £2500,000 transfer in October 1996. 

Adrian played 147 league games for Portsmouth until he suffered a knee injury and, following loans at Luton Town and Reading, left Fratton Park in July 2001 to join Reading on a free transfer. After making eighteen league and cup appearances in 2001/02 Adrian suffered a serious knee injury in December 2001 and didn’t make another first-team appearance prior to arriving at Exeter City on loan in January 2003.

With the Grecians struggling to avoid relegation from the Football League Adrian made his Exeter debut on 23 January 2003 at Macclesfield and appeared seven times up to and including the match against Bournemouth on 23 February 2003. City failed to win any of these games which proved to be the final chapter of Adrian’s professional career as he announced his retirement in April 2003.      

Adrian then joined Barnet as first-team coach with whom he later worked at Brentford, Milton Keynes Dons and Leicester City. He also had spells coaching the Puerto Rico national team as well as managing clubs in Puerto Rico and Antigua and serving as coach to the Bahrain under-23 team. Yet the association with Martin Allen endured and there were returns to Barnet in 2015 and, briefly in March 2018, before the duo took over at Chesterfield between May and December 2018.