| 1. Round | 04/08/2018 | Barrow AFC | - | Havant & Waterlooville | 3:0 | ||||
| 2. Round | 07/08/2018 | Havant & Waterlooville | - | Boreham Wood | 0:0 | ||||
| 10. Round | 08/09/2018 | Harrogate Town | - | Havant & Waterlooville | 3:2 | ||||
| 11. Round | 15/09/2018 | Havant & Waterlooville | - | Sutton United | 1:2 | ||||
| 12. Round | 22/09/2018 | Ebbsfleet United | - | Havant & Waterlooville | 1:1 | ||||
| 13. Round | 25/09/2018 | Barnet FC | - | Havant & Waterlooville | 2:2 | ||||
| 15. Round | 06/10/2018 | Wrexham AFC | - | Havant & Waterlooville | 1:0 | ||||
| 17. Round | 27/10/2018 | Leyton Orient | - | Havant & Waterlooville | 4:0 | ||||
| 18. Round | 30/10/2018 | Havant & Waterlooville | - | Maidenhead United | 7:0 | ||||
| 21. Round | 24/11/2018 | Havant & Waterlooville | - | Maidstone United | 5:2 | ||||
| 38. Round | 12/03/2019 | Havant & Waterlooville | - | Dagenham & Redbridge | 3:0 | ||||
| 39. Round | 16/03/2019 | Havant & Waterlooville | - | Chesterfield FC | 1:2 | ||||
| 45. Round | 22/04/2019 | Aldershot Town | - | Havant & Waterlooville | 2:0 | ||||
| 46. Round | 27/04/2019 | Havant & Waterlooville | - | Barnet FC | 0:2 |
England