 He spent the 1904–05 campaign with Chesterfield, playing 31 Second Division games.After Gilbert Gillies, his manager at Saltergate, was appointed as Leeds City's first manager in March 1905, Ray followed him to Elland Road in July 1905.The club had just been elected to the Second Division and Ray played the club's first-ever Football League appearance in a 1–0 defeat to Bradford City at Valley Parade in September 1905.