For the third cup run, in the 1996–97 season, the first round tie saw Ashford once again meet non-league opposition in the form of Dagenham And Redbridge. Following a 2–2 draw on home turf Ashford visited the 'Daggers' for the replay: the match ended 1–1 but Ashford progressed to the second round by winning 4–3 on penalties, with the vital penalty scored by Paul Chambers, who would later become Ashford United Manager. In the second Round Ashford were drawn away at Watford and they more than matched their higher ranked opponents in a goalless first-half, but eventually the Vicarage Road side ran out 5–0 winners, with substitute David Connolly grabbing a late hat-trick to guide the hosts to victory.