Plymouth, Devon born inside right Ian Gillespie began his career playing for Frost’s Athletic, a youth club associated with Norwich City. He signed for Norwich in 1933 but didn’t feature in their first eleven, prior to signing for Essex & Suffolk Border League club Harwich & Parkeston in 1934. His first known “senior” match was for Harwich in a 3-0 FA Cup First Round defeat at Bristol Rovers in November 1934.
Gillespie signed for Crystal Palace in February 1937 and made his Football League debut at Watford early the next month. He featured 28 times and scored five goals for Palace before the outbreak of the Second World War in September 1939 forced the abandonment of peacetime football and severely disrupted his career, although he also made over 80 wartime league appearances for Palace, also appearing for Ipswich Town. After the War’s end he returned to the Palace first eleven in an FA Cup tie at Queen’s Park Rangers in January 1946 but was sold to Ipswich Town in April 1946, scoring once in 6 appearances for Ipswich in their first post-war League season. However he moved on to Southern League Colchester United in May 1947.
Gillespie made his U’s debut on 17 May in a 2-0 defeat at Bedford Town. He scored his first, and only, league goal in the reverse fixture a week later, on this occasion a 4-0 victory at Layer Road. His final game of 5 first team appearances came on 11th September 1947, a 3-0 Southern League Cup victory over rivals Chelmsford City, a game in which he also scored. After leaving Colchester, Gillespie played for Norfolk & Suffolk League club Leiston.