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.
Ryde's 1899-1900 season was a pivotal moment in their history, as they secured both the Hampshire League and Hampshire Senior Cup titles. Following World War I, Ryde shifted its focus to the Isle of Wight League, where they experienced success by winning the championship twice before returning to their county roots in 1923, when they achieved an easy victory in the East Division.