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.
