|Date of birth||12 November 1969|
|Place of birth||London, England|
|Height||6 ft 0 in (1.83 m)|
|1992||→ Tottenham Hotspur (loan)||10||(0)|
|1995||→ Crystal Palace (loan)||4||(0)|
|1996||→ Bristol City (loan)||6||(1)|
|1996||→ Ipswich Town (loan)||3||(1)|
|2014-||Shirley Town FC||-|
|* Senior club appearances and goals counted for the domestic league only.
† Appearances (Goals).
During his career, Cundy played for Chelsea (1988–92, 41 league appearances), Tottenham Hotspur (loan in 1992, 1992 – November 96, with 28 games), Crystal Palace (one month-loan, 1995), Bristol City (another 30-day loan, 1996), Ipswich Town (after a loan, November 1996–99) and Portsmouth. He was also capped 3 times by England at Under 21 level. In 2014 he signed for Shirley Town FC in the Midland Combination Football League.
Cundy is remembered for the "freak" goal that he scored against Ipswich Town in a Premiership match for Tottenham, in 1992–93. In an attempt to kick the ball 40 yards from goal, he slipped and managed a wind-assisted effort that ended up flying over 'keeper Craig Forrest and into the back of the net. The goal was captured live on Sky Sports and put Spurs 1–0 up, in a match that finished 1–1.
Cundy was forced to retire in 2000 due to a knee injury, and subsequently became a presenter on talkSPORT, regularly appearing with Ian Danter and Alvin Martin on Football First, between 12:00pm–5:00pm. He also occasionally co-hosted Evening Kick-Off, subbing in for any regular member, while appearing regularly as a presenter/pundit on Chelsea TV. He currently co-hosts Andy Goldstein's Sports Bar with Andy Goldstein four of the five weekdays the show airs, with the exception being Fridays when it is co-hosted with Goldstein by Bobby Gould aka the Gouldfather. Jason recently had his hair cut to a number two after him and Goldstein made a bet with a Liverpool F.C. fan, live on air that if Liverpool got in the top 4 in the 2013-14 Premier League season they would both shave their heads. Liverpool manager, Brendan Rodgers was on the line whilst they were having their heads shaved. Cundy is popular for nightly feature 'Wheel Of Cundy' in which he tells a story about a sometimes named and sometimes anonymous footballer he has played with throughout his career.
He also made a TV appearance on the British food programme Ready Steady Cook alongside fellow footballer Graeme Le Saux. The programme was aired on 9 February 2009. In 2010 dancing to Men in Black he appeared on the BBC Let's Dance for Sport Relief with ex-England goalkeeper Peter Shilton. Since March 2011 he has been appearing weekly as a pro pundit on the Facebook football show Scoreboard alongside Scott Minto.
On 11 June 2014, Cundy signed as cover for AFC St Austell, where Cundy's cousin Phil Lafferty is the manager. Due to his media commitments elsewhere however, his appearances for the Lilywhites are to be limited.
Cundy was married to actress/presenter Lizzie Cundy. They divorced in December 2012. The couple has two sons, and they lived in Upton Grey, Hampshire near Odiham. In 1997, Cundy was diagnosed with testicular cancer, from which he later recovered. He is a patron of the Everyman charity.
He is the eldest grandson of Australian tenor Donald Smith.
On Saturday, 18 October 2008, after Cundy did not make it to a TalkSport show, TalkSport radio DJ Andy Goldstein erroneously reported that he had died. The report, which Goldstein later admitted was meant as a joke, resulted in several fans of Chelsea Football Club putting down flowers outside Stamford Bridge the following day.
- Jason Cundy career stats at Soccerbase
- Football - Ex Chelsea and Spurs star signs for St Austell - June 11. http://www.cornishman.co.uk/ .
- Harry Ritchie (13 January 2011) So it's true...great minds DO think alike. Dailymail.co.uk .
- Talksport DJ's sick joke backfires as Chelsea fans lay tributes at Stamford Bridge for 'dead' Jason Cundy. Mirror.co.uk. 20 October 2008.
- The Act Against Bullying Cup 2007. actagainstbullying.com