Billy Gillespie was born in Kerrykeel on the 6th August 1891, the son of a policeman. He began his football career in Derry at the age young age of just 17 and by 1910 Leeds City manager Frank Scott-Walford was persuading him to turn professional. He joined the West Yorkshire club and two years later, Sheffield United signed Gillespie from Leeds City for £500 pounds and the maximum wage of £4 per week. On 22nd December, the Yorkshire Post broke the news that the Irishman would be leaving Elland Road:
"We are informed by Mr Scott-Walford, the Leeds City manager, that he has transferred W Gillespie to Sheffield United at what is stated to be a record fee for the Leeds City club. Gillespie has been regarded as one of the most useful of the Irish brigade at Elland Road. He was secured from the Londonderry Guild club at the beginning of last season, and has played regularly with Leeds City either in the centre-forward or inside-left position. He has played with such success in the latter position that his transfer in the present critical state in the club's affairs may occasion surprise, but ... the management felt, in the circumstances, that they could not reasonably refuse Sheffield United's offer for his transfer…”.
Gillespie was Sheffield United captain from 1923 to 1930 and led the team to its F.A. Cup triumph in 1925 against Cardiff City. Held in such high regard back home, when Gillespie left Sheffield United in 1932 to become player-manager of Derry City, the team changed its strip to red and white 'Candystripe' colours we see today, in reference to his time at Sheffield. He remained at Derry until 1940, taking on the role of full team manager during that time.
Billy's first international cap came in 1913, his two goals giving Ireland their very first victory over England. He was a part of the Ireland side that won the 1914 British Home Championship outright after gaining wins over England and Wales and a draw against Scotland at Windsor Park. According to Ivan Sharpe, a leading sports columnist of the day, Gillespie's “generalship and captaincy for Ireland exceeded even his successes with Sheffield United…Gillespie had the golden gift of piercing a defence with one long, accurate pass”.
Totalling up 25 Irish caps and an international goal haul of 13, he set an Irish record which stood until 2004. He led Derry to two City Cup triumphs and on four successive occasions they finished runners up in the Irish League. Gillespie left an incredible legacy and served as an inspiration to an entire generation of footballers on either side of the Irish Sea. He left Derry City in 1941 and relocated to Bexley in Kent, where he died a month short of his ninetieth birthday in July 1981.