He was first noticed by Burnley when playing for the junior Plymouth Argyle team, the ‘Young Pilgrims’, and he debuted for Burnley at the age of nineteen.  Hillman remained with the club for most of the following decade with the exception of two years with Everton FC, to whom he was sold for £150, where he did not settle and from whom he moved to Dundee briefly who suspended him for ‘not trying’. 

Hillman made one international appearance against Ireland (February 18^th, 1899) with a 13–2 victory for England. When Burnley were struggling to avoid relegation from the First Division, in the 1899 – 1900 season,  their final match against Nottingham Forest had to be won so Hillman offered the, secure opposition, £2 a player to ‘take it easy’ and upped the offer at half time to £5 each.  Burnley lost 4–0 and were relegated.  

He was banned for a season and his action is the first recorded case of attempted match fixing in soccer. He subsequently played for Manchester City (1902 – 1906) and was the goalkeeper in their FA Cup win in 1904.  On his retirement, after yet another ban, he returned to Burnley to run a sweet shop. Hillman had a colourful life outside football, being prosecuted three times for assault but in 1906, he saved the life of a would be suicide by rescuing her from a canal.  One week later, the woman he saved from drowning, a Mrs. Emily Kippax, was prosecuted and convicted of the, then, crime of attempting suicide.