| 2. Ronde | 13.08.2019 | Crusaders FC | - | Warrenpoint Town | 4:0 | ||||
| 3. Ronde | 17.08.2019 | Cliftonville FC | - | Crusaders FC | 0:2 | ||||
| 4. Ronde | 24.08.2019 | Crusaders FC | - | Larne FC | 2:2 | ||||
| 5. Ronde | 31.08.2019 | Crusaders FC | - | Dungannon Swifts | 3:0 | ||||
| 6. Ronde | 07.09.2019 | Institute FC Drumahoe | - | Crusaders FC | 0:6 | ||||
| 7. Ronde | 14.09.2019 | Crusaders FC | - | Glenavon FC | 3:2 |  |
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| 8. Ronde | 21.09.2019 | Coleraine FC | - | Crusaders FC | 4:2 |  |
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| 9. Ronde | 28.09.2019 | Crusaders FC | - | Glentoran FC | 5:2 | |
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| 10. Ronde | 04.10.2019 | Crusaders FC | - | Linfield FC | 1:0 | |
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| 12. Ronde | 19.10.2019 | Crusaders FC | - | Coleraine FC | 0:2 | |
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| 18. Ronde | 30.11.2019 | Dungannon Swifts | - | Crusaders FC | 1:6 | ||||
| 20. Ronde | 14.12.2019 | Glentoran FC | - | Crusaders FC | 1:1 | ||||
| 21. Ronde | 21.12.2019 | Linfield FC | - | Crusaders FC | 1:1 | ||||
| 22. Ronde | 26.12.2019 | Crusaders FC | - | Cliftonville FC | 1:2 | |
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| 29. Ronde | 03.03.2020 | Crusaders FC | - | Cliftonville FC | 0:0 | |
Noord-Ierland