Richard Dryden, signing from Bristol Rovers, made thirty league appearances as Exeter City won the Division Four title in 1989/90. Later playing for clubs such as Notts County, Birmingham City, Southampton, Bristol City and Luton Town he remained in the game in a variety of coaching and management roles often in partnership with former Exeter teammate Mark Cooper.      

Richard started his career in 1986 as a trainee with Bristol Rovers and, after signing professional in July 1987, went on to make thirteen league appearances for the club. Initially joining Exeter City on loan in September 1988, featuring in six games appearances in a two-month stay, Richard moved to St James’ Park on a permanent basis in March 1989 for a basic fee of £10,000 plus various add-on clauses. 

Playing in the final fifteen games of 1988/89 as Terry Cooper’s side started to take shape, Richard went on to score seven times from thirty starts as City landed the Fourth Division title in 1989/90.

Richard’s form now attracted the attention of other clubs as he added another half-a-dozen league goals in the third-tier in 1990/91. With the amount due to Bristol Rovers now growing, Exeter had already turned down a £60,000 bid from Rotherham United in January 1991 when Richard was allowed to join Manchester City on loan in the summer of 1991 with a possible transfer in mind. As nothing arose from this, an offer of £250,000 (plus add-ons) was accepted from Notts County in August 1991. 

With Notts playing top-flight football in 1991/92, Richard’s opportunities were relatively limited and, following a loan stint with Plymouth Argyle, he moved to Birmingham City for £165,000 in March 1993 where he was reunited with Terry Cooper. His next move was to Bristol City in December 1994 for £140,000 before a switch to Southampton in a £150,000 deal in August 1996.  Loaned to Stoke City, Northampton Town and Swindon while at Southampton, Richard joined Luton in 2001 ahead of moving to Scarborough (by now back in the Conference) as his professional career drew to a close.   

Richard then appeared for Worksop Town ahead of his appointment as former Exeter teammate Mark Cooper’s assistant at Tamworth between April 2004 and January 2007. Next, after playing for Shepshed Dynamo and managing Worcester City, Richard worked with Mark Cooper again at Darlington from June 2010 to February 2011. 

He was then head of youth at York City prior to assuming various roles at Notts County where he was to be joined by Mark Cooper when his old teammate arrived as manager in 2016. Now assistant manager, Richard wasn’t in post for long before both were sacked leading him to take a management position with Kingfisher East Bengal in India followed by scouting roles with Forest Green Rovers (on behalf of Mark Cooper), Bury and - during 2019/20 - Leyton Orient. 

Richard then had a stint as Mark Cooper's assistant manager at Barrow before, after time away from the game, his appointment as assistant manager of Aldershot Town in April 2023.