| 1. Round | 04/08/2018 | Dungannon Swifts | - | Ballymena United | 0:2 | ||||
| 2. Round | 10/08/2018 | Newry City FC | - | Dungannon Swifts | 2:1 | ||||
| 3. Round | 18/08/2018 | Dungannon Swifts | - | Cliftonville FC | 1:1 | ||||
| 4. Round | 25/08/2018 | Glentoran FC | - | Dungannon Swifts | 2:1 | ||||
| 5. Round | 01/09/2018 | Institute FC Drumahoe | - | Dungannon Swifts | 0:0 | ||||
| 7. Round | 15/09/2018 | Linfield FC | - | Dungannon Swifts | 3:0 | ||||
| 8. Round | 22/09/2018 | Dungannon Swifts | - | Ards FC | 0:0 | ||||
| 6. Round | 25/09/2018 | Dungannon Swifts | - | Crusaders FC | 3:2 | ||||
| 9. Round | 29/09/2018 | Glenavon FC | - | Dungannon Swifts | 2:1 | ||||
| 10. Round | 06/10/2018 | Dungannon Swifts | - | Warrenpoint Town | 0:2 | ||||
| 13. Round | 27/10/2018 | Dungannon Swifts | - | Linfield FC | 1:2 | ||||
| 14. Round | 03/11/2018 | Ards FC | - | Dungannon Swifts | 2:2 |  |
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| 15. Round | 10/11/2018 | Dungannon Swifts | - | Institute FC Drumahoe | 2:1 | ||||
| 16. Round | 17/11/2018 | Warrenpoint Town | - | Dungannon Swifts | 1:1 | ||||
| 17. Round | 24/11/2018 | Dungannon Swifts | - | Glentoran FC | 1:0 |
Northern Ireland