20 Juli 2019
League Cup:: group H
20 Jul  
21:00'
East Kilbride
? - ?
St. Mirren
21:00'
Edinburgh City
? - ?
Dunfermline Athletic
Scotland - League Cup:: group A
20 Jul  
01:45'
Dundee United
? - ?
Cowdenbeath
21:00'
East Fife
? - ?
Stenhousemuir
Scotland - League Cup:: group B
20 Jul  
21:00'
Montrose
? - ?
Forfar Athletic
Scotland - League Cup:: group C
20 Jul  
21:00'
Elgin City
? - ?
Stirling Albion
21:00'
Hibernian
? - ?
Alloa Athletic
Scotland - League Cup:: group D
20 Jul  
21:00'
Dundee FC
? - ?
Peterhead
21:00'
Inverness CT
? - ?
Raith Rovers
Scotland - League Cup:: group E
20 Jul  
01:45'
Motherwell
? - ?
Greenock Morton
21:00'
Dumbarton
? - ?
Queen of South
Scotland - League Cup:: group F
20 Jul  
21:00'
Hamilton Academical
? - ?
Partick Thistle
Scotland - League Cup:: group G
20 Jul  
21:00'
Ayr United
? - ?
Falkirk
21:00'
Stranraer
? - ?
Berwick Rangers
21 Juli 2019
League Cup:: group B
21 Jul  
FT'
St. Johnstone
1 - 2
Ross County
Scotland - League Cup:: group F
21 Jul  
FT'
Clyde
2 - 3
Airdrieonians
24 Juli 2019
League Cup:: group H
24 Jul  
01:45'
Albion Rovers
? - ?
St. Mirren
01:45'
Edinburgh City
? - ?
East Kilbride
Scotland - League Cup:: group A
24 Jul  
01:45'
Dundee United
? - ?
East Fife
Scotland - League Cup:: group C
24 Jul  
01:45'
Alloa Athletic
? - ?
Stirling Albion
01:45'
Hibernian
? - ?
Arbroath
Scotland - League Cup:: group D
24 Jul  
01:45'
Inverness CT
? - ?
Cove Rangers
01:45'
Raith Rovers
? - ?
Peterhead
Scotland - League Cup:: group E
24 Jul  
01:45'
Annan Athletic
? - ?
Greenock Morton
01:45'
Dumbarton
? - ?
Motherwell
Scotland - League Cup:: group G
24 Jul  
01:45'
Berwick Rangers
? - ?
Falkirk
01:45'
Stranraer
? - ?
Livingston