Cockfield, County Durham born centre forward Jack Holliday started his football career with Cockfield in 1929 and signed for First Division club Middlesbrough in 1930, scoring twice on his Football League debut at Manchester City in November of that year. But opportunities were limited behind George Camsell in the pecking order and he only played 6 times over two seasons scoring 4 goals before joining Division Three (South) club Brentford in May 1932.
His first season at Griffin Park saw 38 goals in 34 League games as they won the League Championship, still Brentford’s club record for most goals in a season, and he scored all 5 goals in a 5-5 draw at Luton Town in February 1933 as well as 4 goals against Cardiff City in April 1933 and hat-tricks against Newport County, Clapton Orient and Gillingham. After 27 goals in 1933-34 as they finished fourth in the Second Division, he scored 25 goals as they were promoted to the First Division as Second Division Champions in 1935, with hat-tricks against West Ham United, Burnley and Port Vale.
Although his scoring rate reduced in the top flight as he moved to inside left to accomodate Dave McCulloch at centre forward, he scored 13 goals as Brentford finished in an all time best fifth in the League Championship in 1935-36, and he continued to play until the outbreak of the Second World War in September 1939, retiring in 1944 after playing wartime football for Brentford, remaining at Brentford on the coaching staff until May 1961. He totalled 120 goals in 224 (peacetime) appearances for The Bees.