Sherwood came agonisingly close to major silverware in 1984 when his Watford were beaten by Everton in the final of the FA Cup. Although the goalkeeper began his career at Chelsea, he spent his prime years with the Hornets, making 211 appearances between the sticks.
He began his second career at Allied Dunbar after meeting two former Leeds players who had made a similar transition, before moving on to Standard Life in 2001. He is now an IFA with Positive Solutions, based in Grimsby, where he also used to play for the local club.
Darren Ward - Defender
Although still very much an integral part of the Millwall setup, Darren Ward has always had an eye on life beyond football, director and shareholder of New Incentive Financial Consultants, and is an introducer of Finsbury Financial.
His younger brother Elliott plays for Norwich City, while two other brothers previously played professional football.
Helping him stand out from the other footballer/advisers is his ownership of a cattery in Hertfordshire. Although he has a few playing years left in him, Ward seems well-prepared for life after The Beautiful Game.
David Rowson - Midfield
Currently in his second stint at Partick Thistle, Rowson has previously played for Aberdeen and Northampton in a career stretching back to 1994. Although not registered with the FSA at the moment, he has a Certificate in Financial Planning and is currently working towards his Level 4 qualifications.
He did work as a financial adviser at Premier Financial Management in Scotland in 2009, but only managed eight months before football commitments meant he had to leave.
However, under a new contract he is planning scale back his training hours in order to spend the rest of the time working as an IFA.
Paul Ware - Midfield
Beginning his career at Stoke City, Ware played 115 games for the Potters before a stints at Stockport County and Macclesfield Town. After a few more years with clubs in the north, he finished his playing career at non-league Hednesford Town.
For almost a decade now, he has been involved in the world of financial advice and, following spells at Lloyds TSB and Barclays, he is now an IFA at Wayne Austin. He is currently working towards Chartered Status.
Paul Mullin - Striker
Mullin appeared more than 450 times and scored almost 200 goals for Accrington Stanley, during which the club made its way from the lower leagues in to the fourth tier of the game.
Now a chartered financial planner with Bolton-based Pro Sport Wealth Management, he maintains a strong connection to his previous profession through a deal with the PFA to provide financial advice to 36 clubs spanning the Championship - English football's second tier - to League Two.