Blackburn, Lancashire born outside left Herbert ‘Tiddler’ Ashton began his football career with Padiham in 1903 and joined Lancashire Combination club Accrington Stanley in 1904. He signed for First Division Preston North End in 1905, making his Football League debut against Bolton Wanderers in April 1906, making a pair of appearances in each of April 1906 and the spring of 1907 before returning to Accrington Stanley in the 1907 close season.
Ashton signed for Southern League West Ham United in 1908, making his debut in a 2-0 win against Queens Park Rangers on 1st September 1908. A firm fans’ favourite and small in stature he was rarely without support from the fans when things got rough on the pitch, even to the extent of invading the pitch to protect Ashton in a match against New Brompton. Ashton holds the record for the most appearances in the Southern League for West Ham with 224 appearances out of a total of 249 appearances, in which he scored 24 goals until the suspension of peacetime football due to the onset of the First World War in the summer of 1915.
Ashton joined the Royal Flying Corps as a mechanic during the First World War whilst still playing football for West Ham in the London Combination League but retired soon the end of the War, playing his final match for West Ham in a wartime league match against Millwall in April 1919, having scored 11 goals in 87 wartime matches for The Hammers.