Speelronde 1
Toeschouwers:
Scheidsrechter:
Scoreverloop:
Rugby Park
Kilmarnock F.C. 
14:30 
Rangers F.C.
14:30 Rangers F.C.18-07-2019 Kilmarnock F.C. vs Connah’s Quay Nomads F.C.
Heenwedstrijd 2-1
Toeschouwers: 8.306.
Scheidsrechter: Ferenc Karakó (Hongarije).
Scoreverloop:
0-1 Callum Morris 50. (assist Ryan Wignall)
0-2 Callum Morris 80. (strafschop)
Kilmarnock F.C.: Rory McKenzie (65), Connah’s Quay Nomads F.C.: John Disney (34), Michael Wilde (60), Danny Holmes (78), Jamie Insall (83)
Connah’s Quay Nomads F.C.: Ryan Wignall (85)
Kilmarnock F.C.: Stuart Findlay (79)
Connah’s Quay Nomads F.C.19-05-2019 Kilmarnock F.C. vs Rangers F.C.
Kilmarnock F.C. 2 vs 1 Rangers F.C.
2 vs 1 Rangers F.C.11-05-2019 Kilmarnock F.C. vs Hibernian F.C.
Kilmarnock F.C. 1 vs 0 
Hibernian F.C.
1 vs 0 Hibernian F.C.20-04-2019 Kilmarnock F.C. vs Aberdeen F.C.
Kilmarnock F.C. 0 vs 1 
Aberdeen F.C.
0 vs 1 Aberdeen F.C.06-04-2019 Kilmarnock F.C. vs St. Johnstone F.C.
St. Johnstone F.C.30-03-2019 Kilmarnock F.C. vs Hamilton Academical F.C.
Hamilton Academical F.C.02-03-2019 Kilmarnock F.C. vs Motherwell F.C.
Kilmarnock F.C. 0 vs 0 
Motherwell F.C.
0 vs 0 Motherwell F.C.17-02-2019 Kilmarnock F.C. vs Celtic F.C.
Kilmarnock F.C. 0 vs 1 
Celtic F.C.
0 vs 1 Celtic F.C.
Heart of Midlothian F.C.