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 West Ham United and made his debut against Queen's Park Rangers on 1st September 1908. He was extremely small and was therefore nicknamed "Tiddler" by the fans.
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.