Fencehouses, County Durham born outside right Cyril Gilhespy began his football career playing for Chester-le-Street immediately after the end of the First World War, and he also played for Fencehouses in 1919 before signing for First Division club Sunderland in August 1920, for whom he made his Football League debut against Bradford City that October. He scored once in 15 appearances for The Wearsiders before being signed by Liverpool for £250 in August 1921. He spent four seasons at Anfield mainly as understudy to Bill Lacey, and played 10 League matches in 1922-23 at Liverpool won the League Championship for a second season running, but after 3 goals in 19 appearances he joined Third Division (South) club Bristol City in May 1925, at the time managed by former Liverpool stalwart Alex Raisbeck.
Gilhespy made his debut for The Robins at outside right in a 1-0 defeat to Norwich City on 29th August 1925, making 35 appearances and scoring 6 goals in his first season at Ashton Gate. When Bristol City finished winners of the Third Division (South) Championship in 1926-27 Gilhespy made 40 appearances scoring 8 goals including one in the 9-4 victory over Gillingham on 15th January 1927 when Tot Walsh netted a record six goals.
The following season in the Second Division Gilhespy began by scoring in each of the opening five games including a brace in a 4-1 win at Grimsby Town but made only 14 appearances scoring 7 goals, however he returned to being a regular fixture in The Robins’ team from September 1928, and did enough to earn a return to top flight football when he was signed by Blackburn Rovers in June 1929 after 25 goals in 118 appearances for Bristol City. He had a single season at Ewood Park, scoring once in 5 appearances, before joining Reading in June 1930 for whom he scored 4 goals in 24 appearances as The Royals suffered relegation from the Second Division at the season’s end.
Already well into his 30’s, Mansfield Town paid £150 for Gilhespy in August 1931, where he spent a further season, scoring 4 goals in 20 appearances, before joining Crewe Alexandra in August 1932. where he made a final 3 appearances in the autumn of 1932 before retiring from professional football.