During his career, Cundy played for Chelsea (198892, 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 199699) and Portsmouth. He was also capped 3 times by England at Under 21 level.
Cundy is remembered for the "freak" goal that he scored against Ipswich Town in a Premiership match for Tottenham, in 199293. 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 10 up, in a match that finished 11.
Cundy is remembered for the "freak" goal that he scored against Ipswich Town in a Premiership match for Tottenham, in 199293. 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 10 up, in a match that finished 11.