The 1899-1900 season was a highly successful one in which they won the Hampshire League and Hampshire Senior Cup double. After the Great War, Ryde joined the Isle of Wight League, twice being champions before returning the county fold in 1923 when they promptly won the East Division title at the first attempt.
The 1899-1900 season was a standout year for Ryde, as they claimed both the Hampshire League and Hampshire Senior Cup championships. Following World War I, Ryde transitioned to the Isle of Wight League, where they achieved back-to-back titles before returning to their county affiliation in 1923, when they dominated the East Division.