Herbert Ashton was born in Blackburn in 1887. He played football for Accrington Stanley before joining Preston North End. He only played in four games in the 1905-06 season before returning to Accrington.
Ashton joined a team that included Jack Foster, William Yenson, Tommy Allison, Fred Blackburn, George Chalkley, Billy Grassam, Alfred Harwood, Len Jarvis, George Kitchen, Frank Piercy, Tommy Randall, Danny Shea, George Webb and Robert Young. Ashton played in 27 games that season.
Ashton played in every West Ham United league game in the 1909-10 season. He became a great favourite with the Upton Park fans. Tony Hogg wrote in Who's Who of West Ham United: "As his nickname would indicate, Herbert was small in stature, but the diminutive winger had plenty of fans ready to help him out when the going got rough, a section of whom took their protective instincts too far when they invaded the pitch to do battle on their hero's behalf in a particularly tough Upton Park encounter with Syd King's old team, New Brompton."
The outside-right kept his place for the next few seasons. However, he was never a prolific goalscorer. His record was 1909-10 (4 in 42), 1910-11 (6 in 37), 1911-12 (3 in 23), 1912-13 (6 in 36) and 1913-14 (3 in 35). In all, he played in 229 league and cup games for West Ham United.
Attendances at league games fell dramatically during the second-half of the 1914-15 season because of the impact of the First World War. It was decided that the Southern League would not operate in the 1915-16 season. As football players only had contracts to play for one season at a time, they were now out of work. It has been estimated that around 2,000 of Britain's 5,000 professional footballers now joined the armed forces. This included Ashton who became a mechanic in the Royal Flying Corps.