David Webb was born in Stratford (then in Essex) and began his career as an amateur with West Ham United, but on failing to make the grade joined Leyton Orient in May 1963.
He scored twice in 75 games for the Saints, including a goal on his debut to equalise in a vital 1–1 draw at promotion rivals Wolverhampton Wanderers, before joining Chelsea in February 1968.
During the first game at Wembley, Webb, playing at right-back, had a nightmare and was tormented throughout the match by the nimble and tricky Leeds winger Eddie Gray as Chelsea were somewhat fortunate to emerge with a 2–2 draw.
Manager Dave Sexton made a tactical switch for the replay, moving Webb to the centre to partner John Dempsey while the more uncompromising Ron Harris was detailed to mark Gray.
Webb – and Chelsea overall – performed markedly better in the replay and it was he who proved the unlikely hero, heading in the winner from an Ian Hutchinson throw-in in extra time.
Although he spent much of his Chelsea career as a right back, he also played in central defence (his original position) and occasionally as a centre forward, once hitting a hat-trick against Ipswich Town in December 1968.
Ipswich were once again witness to his versatility when he played as a goalkeeper for an entire match, on 27 December 1971, keeping a clean sheet in the process, and then scored two goals in the return fixture as a centre forward in March 1972.
[citation needed] In February 1984, after a spell out of the game working as a self-employed salesman, he was appointed manager of Torquay United in succession to Bruce Rioch.
His spell in charge is not fondly remembered, the team had two disastrous seasons; five of United's key players were released as soon as he took over, others such as Keith Curle were sold cheaply, and replaced by vastly inferior players, and the club colours changed to blue..[citation needed] Webb left Torquay to manage Southend United, another Fourth Division side, on 17 June 1986.