3e Ronde
06.09.2019 20:45 Waterford FC Waterford FC - Heart of Midlothian (R) 3:1 (1:0)
07.09.2019 14:00 Airdrieonians Airdrieonians - Bohemian FC Bohemian FC 3:2 (1:1)
07.09.2019 16:00 Stenhousemuir FC Stenhousemuir FC - The New Saints The New Saints 3:1 (0:0, 1:1) d.p.
07.09.2019 16:00 Wrexham AFC Wrexham AFC - Ayr United Ayr United 6:5 (0:0, 1:1) d.p.
07.09.2019 16:00 Kelty Hearts - Solihull Moors Solihull Moors 2:4 (1:0, 1:1) d.p.
07.09.2019 16:00 Formartine United Formartine United - Glenavon FC Glenavon FC 0:3 (0:1)
07.09.2019 16:00 Inverness CT Inverness CT - Greenock Morton FC Greenock Morton FC 3:1 (2:0)
07.09.2019 16:00 Montrose FC Montrose FC - Partick Thistle Partick Thistle 0:2 (0:1)
07.09.2019 16:00 St. Mirren FC (R) - Stirling Albion FC Stirling Albion FC 1:0 (0:0)
07.09.2019 16:00 Dundee United Dundee United - Arbroath FC Arbroath FC 3:4 (0:0, 0:0) d.p.
07.09.2019 16:00 Clyde FC Clyde FC - Queen Of The South Queen Of The South 3:2 (0:1)
07.09.2019 16:00 Raith Rovers Raith Rovers - Falkirk FC Falkirk FC 2:0 (1:0)
07.09.2019 16:00 Dunfermline Athletic Dunfermline Athletic - Alloa Athletic Alloa Athletic 1:2 (1:1)
07.09.2019 18:15 Connah's Quay Nomads Connah's Quay Nomads - Cove Rangers Cove Rangers 1:0 (0:0)
08.09.2019 16:00 Dundee FC Dundee FC - Elgin City Elgin City 1:2 (1:0)
18.09.2019 20:45 Ballymena United Ballymena United - Rangers FC (R) -:-
4e Ronde
12.10.2019 Arbroath FC Arbroath FC - Clyde FC Clyde FC -:-
12.10.2019 Airdrieonians Airdrieonians - Elgin City Elgin City -:-
12.10.2019 Raith Rovers Raith Rovers - Glenavon FC Glenavon FC -:-
12.10.2019 Partick Thistle Partick Thistle - Connah's Quay Nomads Connah's Quay Nomads -:-
12.10.2019 Wrexham AFC Wrexham AFC - St. Mirren FC (R) -:-
12.10.2019 Stenhousemuir FC Stenhousemuir FC - Waterford FC Waterford FC -:-
12.10.2019 Solihull Moors Solihull Moors - Ballymena / Rangers (R) -:-
12.10.2019 Inverness CT Inverness CT - Alloa Athletic Alloa Athletic -:-
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