| 9. Round | 03/06/2023 | Rīgas Futbola skola II | - | JFK Ventspils | 2:0 | ||||
| 12. Round | 22/07/2023 | JFK Ventspils | - | Beitar Rīga | 0:1 | ||||
| 13. Round | 30/07/2023 | Skanstes SK | - | JFK Ventspils | 2:1 | ||||
| 15. Round | 13/08/2023 | AFA Olaine | - | JFK Ventspils | 1:1 |  |
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| 16. Round | 20/08/2023 | JFK Ventspils | - | Riga FC II | 0:0 | |
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| 17. Round | 27/08/2023 | FK Smiltene | - | JFK Ventspils | 1:1 | ||||
| 18. Round | 02/09/2023 | JFK Ventspils | - | Grobiņas SC | 0:2 | ||||
| 19. Round | 16/09/2023 | Saldus SS/Leevon | - | JFK Ventspils | 0:1 | ||||
| 21. Round | 30/09/2023 | FK Tukums 2000 II | - | JFK Ventspils | 1:1 | ||||
| 24. Round | 28/10/2023 | JFK Ventspils | - | JDFS Alberts | 2:3 | ||||
| 25. Round | 04/11/2023 | Beitar Rīga | - | JFK Ventspils | 0:4 | ||||
| 26. Round | 12/11/2023 | JFK Ventspils | - | Skanstes SK | 0:1 |
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