The three matches at Hampden Park were played behind closed doors due to Scottish Government restrictions.
The draw for the preliminary rounds took place on Thursday, 18 July 2019 at Hampden Park and was made by Scotland internationals Lee Alexander and Leanne Crichton.
Blackburn United, Broxburn Athletic, Dundonald Bluebell, Easthouses Lily Miners Welfare, Hill of Beath Hawthorn, Jeanfield Swifts, and Penicuik Athletic took part in the Scottish Cup for the first time having each gained their Club Licence, along with Camelon Juniors who made their debut as 2018–19 South & East Cup-Winners Shield winners.
The final part of the draw saw seven ties drawn in the second preliminary round to be played on Saturday, 31 August 2019.
[8] The draw for the second round took place on Sunday 22 September 2019 during Sportscene live on BBC Scotland and was made by Kenny Miller and Kris Doolan.
[8] The draw for the fourth round took place on Sunday 24 November 2019 during Sportscene live on BBC Scotland.
[92] Broxburn Athletic, the lowest ranked team left in the competition, were drawn against Premiership club St Mirren (54 places above them), which at the time represented the biggest league position gap between two teams in the competition's history since the pyramid system was introduced.
Following on from a campaign in England's FA Cup, all matches kicked-off one minute later than originally scheduled to raise awareness and encourage supporters to talk about their mental health.
The draw for the quarter-finals took place on Sunday 9 February 2020 following the Clyde-Celtic match live on Premier Sports 1.
The semi-finals were originally scheduled to take place at Hampden Park over the weekend of 11 April 2020 but were postponed due to the COVID-19 pandemic.
[3] The draw for the semi-finals took place on Sunday 1 March 2020 following the St Johnstone-Celtic match live on Premier Sports 1.
[130][131] The final was originally scheduled to be played on 9 May 2020 at Hampden Park in Glasgow, but was postponed due to the coronavirus pandemic.