The winners of each of the eight groups, as well as the four best runners-up progressed to the second round (last 16), which includes the four UEFA qualifying clubs.
In December 2015, the SPFL announced that alongside the new group stage format, a bonus point system would be introduced to provide greater excitement and increase the number of meaningful games at this stage.
The draw for the group stage took place on 28 May 2019 and was broadcast live on the SPFL YouTube channel.
The draw for the second round took place on 28 July 2019 at the conclusion of the Dundee-Inverness Caledonian Thistle match.
The domestic broadcasting rights for the competition are held exclusively by BT Sport.