The 2019–20 season saw Harrogate Town finish second in the National League, and thus qualified for the play-offs.

[1] They defeated Boreham Wood 1–0 in the semi-final,[2] before a 3–1 victory over Notts County in the final secured Harrogate's promotion to the Football League for the first time in their history.

[3] Since the EFL require all matches to be played on grass pitches, the club played all their home matches for the first month of the season at Doncaster Rovers' Keepmoat Stadium whilst the club replaced their synthetic pitch at Wetherby Road.

[86] The first round draw was made live on Sky Sports on 18 August 2020, with Harrogate being drawn away to fellow League Two side Tranmere Rovers, with the match set to be played on 5 September 2020.

[89] The draw for both the second and third round were confirmed on September 6, live on Sky Sports by Phil Babb.