4. Runde
11.10.2019 20:35 Stenhousemuir FC Stenhousemuir FC - Waterford FC Waterford FC 3:2 (1:1)
12.10.2019 16:00 Arbroath FC Arbroath FC - Clyde FC Clyde FC 0:2 (0:1)
12.10.2019 16:00 Airdrieonians Airdrieonians - Elgin City Elgin City 0:2 (0:0)
12.10.2019 16:00 Raith Rovers Raith Rovers - Glenavon FC Glenavon FC 3:1 (2:1)
12.10.2019 16:00 Wrexham AFC Wrexham AFC - St. Mirren FC (R) 4:1 (0:0)
12.10.2019 16:00 Inverness CT Inverness CT - Alloa Athletic Alloa Athletic 3:0 (1:0)
12.10.2019 18:15 Partick Thistle Partick Thistle - Connah's Quay Nomads Connah's Quay Nomads 2:0 (1:0)
29.10.2019 20:45 Solihull Moors Solihull Moors - Rangers FC (R) -:-
Viertelfinale
16.11.2019 Inverness CT Inverness CT - Clyde FC Clyde FC -:-
16.11.2019 Raith Rovers Raith Rovers - Elgin City Elgin City -:-
16.11.2019 Solihull / Rangers (R) - Wrexham AFC Wrexham AFC -:-
16.11.2019 Stenhousemuir FC Stenhousemuir FC - Partick Thistle Partick Thistle -:-