| 1. Round | 15/02/2020 | Bohemian FC | - | Shamrock Rovers | 0:1 | ||||
| 2. Round | 21/02/2020 | Shamrock Rovers | - | Cork City | 6:0 | ||||
| 5. Round | 07/03/2020 | Sligo Rovers | - | Shamrock Rovers | 2:3 | ||||
| 6. Round | 01/08/2020 | Shamrock Rovers | - | Finn Harps | 3:1 | ||||
| 7. Round | 09/08/2020 | Derry City | - | Shamrock Rovers | 1:2 |  |
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| 8. Round | 16/08/2020 | St Patrick's Athletic | - | Shamrock Rovers | 0:0 | ||||
| 9. Round | 21/08/2020 | Shamrock Rovers | - | Shelbourne FC | 0:0 | ||||
| 10. Round | 05/09/2020 | Shamrock Rovers | - | Bohemian FC | 1:0 | |
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| 11. Round | 12/09/2020 | Cork City | - | Shamrock Rovers | 0:3 | ||||
| 12. Round | 21/09/2020 | Shamrock Rovers | - | Waterford FC | 6:1 | ||||
| 13. Round | 27/09/2020 | Dundalk FC | - | Shamrock Rovers | 0:4 | ||||
| 14. Round | 02/10/2020 | Shamrock Rovers | - | Sligo Rovers | 4:0 |
Ireland