A forward, Holliday joined hometown club Middlesbrough in March 1930. Behind George Camsell in the pecking order, he spent most of his time in the club's reserve team. He won the North Eastern League title in the 1930–31 and 1931–32 seasons and scored 78 goals during the latter season. Despite these exploits, Holliday rarely featured at first team level, but managed to score four goals in six First Division appearances. He departed Ayresome Park in May 1932.
Brentford
Holliday and Middlesbrough teammates Billy Scott and Bert Watson moved to join Third Division South club Brentford in May 1932. He flourished under Harry Curtis' management and scored 39 goals in 35 games to send the Bees to the Second Division as 1932–33 Third Division South champions. With 38 league goals, he set the club record for most league goals scored in a season and most league hat-tricks in a season, records which as of 2018 have never been surpassed. He was also the first player to score five goals in a single game for Brentford, which he achieved in a 5–5 draw with Luton Town on 1 February 1933. The Bees narrowly missed out on a second successive promotion during the 1933–34 season and finished fourth in the Second Division, with Halliday scoring 27 goals from 41 appearances. His 25 goals during the 1934–35 season helped Brentford to the Second Division championship and to promotion to the top tier of English footballfor the first time in the club's history. Holliday's goalscoring form in the First Division failed to meet the heights of previous seasons, but he still managed 13 goals from 38 appearances during the 1935–36 season, which culminated in Brentford's highest-ever league placing of fifth. Holliday was eventually converted into a Utility player by manager Curtis and stayed with the Bees throughout the remainder of the 1930s. He played his last professional game for the club on the final day of the 1938–39 season, a 2–0 defeat to Arsenal at Highbury. The breakout of the Second World Warin September 1939 saw professional football suspended, but Holliday remained with the club through the war years and made his final appearance against Reading on the final day of the 1943–44 season. In seven years of competitive football with Brentford, Holliday scored 119 goals in 223 games. Only two players have surpassed Holliday's goalscoring record for the club and his 9 hat-tricks in league matches is a club record.
International career
Holliday's form during the 1934–35 season saw him called up to represent an England XI in a friendly versus an Anglo-Scots team at Highbury on 8 May 1935. His England team suffered a 1–0 defeat.
Coaching career
After his retirement from football in 1944, Holliday remained with Brentford and served as a trainer to the senior and reserve teams until May 1961.
Personal life
Holliday's father James was an amateur footballer and was killed during the First World War.HonoursMiddlesbrough Reserves
