The 1960–61 campaign saw the club's FA Cup exploits curtailed once again in the First Round proper with a 1–2 home loss (Town scorer: Joe White) to League club Gillingham. On the Gills teamsheet was forward John Shepherd who played for and skippered Ashford the following season. The cup run in that 1961–62 season was the next high-point in Ashford Town's history when the club reached the FA Cup 2nd round proper. After beating (then non-league) Wycombe Wanderers 3–0 (scorers Joe White, Ron Clayton & John Shepherd) in a First Round replay at Essella Park, the club lost 0–3 on home turf to Queens Park Rangers – playing for the visitors was Keith Rutter who would subsequently return to Ashford three years later to captain the team.