Education
The goal was captured live on Sky Sports and put Spurs 1–0 up, in a match that finished 1–1.
The goal was captured live on Sky Sports and put Spurs 1–0 up, in a match that finished 1–1.
He also presented "You"re On Sky Sports" for a period of time. During his career, Cundy played for Chelsea (1988-1992, 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 1996-1999) and Portsmouth. He was also capped 3 times by England at Under 21 level
In 2014 he signed for Shirley Town Football Club 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 1992-1993. 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 Netto.
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-Office, subbing in for any regular member, while appearing regularly as a presenter/pundit on Chelsea television 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 2013-2014 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 football player he has played with throughout his career. He also made a television appearance on the British food programme Ready Steady Cook alongside fellow football player Graeme Le Saux.
The programme was aired on 9 February 2009.
In 2010 dancing to Men in Black he appeared on the British Broadcasting Corporation 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.
Due to his media commitments elsewhere however, his appearances for the Lilywhites are to be limited.
