| 1. Round | 14/02/2020 | Cork City | - | Shelbourne FC | 0:1 | ||||
| 2. Round | 21/02/2020 | Shelbourne FC | - | Dundalk FC | 1:2 |  |
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| 6. Round | 01/08/2020 | Shelbourne FC | - | Waterford FC | 0:1 | ||||
| 3. Round | 04/08/2020 | Finn Harps | - | Shelbourne FC | 0:1 | ||||
| 7. Round | 08/08/2020 | Sligo Rovers | - | Shelbourne FC | 2:1 | ||||
| 8. Round | 15/08/2020 | Shelbourne FC | - | Derry City | 1:1 | |
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| 9. Round | 21/08/2020 | Shamrock Rovers | - | Shelbourne FC | 0:0 | ||||
| 10. Round | 05/09/2020 | Shelbourne FC | - | Cork City | 1:1 | ||||
| 11. Round | 11/09/2020 | Dundalk FC | - | Shelbourne FC | 3:2 | ||||
| 12. Round | 19/09/2020 | Shelbourne FC | - | Finn Harps | 1:1 | ||||
| 13. Round | 26/09/2020 | St Patrick's Athletic | - | Shelbourne FC | 2:0 | |
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| 14. Round | 03/10/2020 | Shelbourne FC | - | Bohemian FC | 1:3 | ||||
| 15. Round | 10/10/2020 | Waterford FC | - | Shelbourne FC | 0:1 | |
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| 16. Round | 18/10/2020 | Shelbourne FC | - | Sligo Rovers | 1:0 | ||||
| 17. Round | 23/10/2020 | Derry City | - | Shelbourne FC | 2:0 | ||||
| 18. Round | 09/11/2020 | Shelbourne FC | - | Shamrock Rovers | 0:2 |
Ireland