They finished as runners up in the league no less than four times during the 1930s and in the 1933–34 season reached the semi-finals of the G.F A Senior Amateur Cup, losing to Victoria Albion at the Douglas Ground, Kingswood.

A period of rebuilding followed which took longer than anticipated as there were a limited number of players in the villages of Winterbourne, Watleys End and Frampton Cotterell.

During that season strength of the club was evident as the Reserves team won the Bristol & District League First Division title and also carried off both the Premier and Senior Berkeley Hospital Cups.

A poor season in 1995–96 saw the Club relegated from the Gloucestershire County League back to the Bristol Premier Combination despite reaching the G.F.A.

Senior Amateur Cup, they clinched promotion by winning the Premier Combination championship by 7 clear points from their nearest rivals Hambrook.

Winterbourne also has a successful 'A' team in Division 3 of the Bristol and District League consisting of the younger element bonded together by a few experienced old stagers.