| 2023/10/14 | Nomme Kalju |  | 3-1 |  | Harju JK | ||||
| 2023/10/18 | Läänemaa JK |  | 9-1 |  | Arukula | ||||
| 2023/11/18 | Viimsi |  | 1-0 |  | Narva Trans | ||||
| 2023/11/24 | Paide LM |  | 4-0 |  | Kalev Tallinn B | ||||
| FCI Levadia |  | 4-2 |  | JK Tammeka | |||||
| 2023/11/25 | Kuressaare |  | 4-2 |  | FC Flora B | ||||
| 2023/11/26 | Kalev Tallinn | | 3-1 |  | FC Nõmme United | ||||
| 2023/12/03 | FC Flora | | 10-0 |  | Elva |
| 2023/08/16 | Tartu Kalev |  | 2-6 | | FCI Levadia | ||||
| 2023/08/22 | Elva | | 5-2 |  | JK Tervis Parnu | ||||
| FC Nõmme United | | 11-1 |  | Eston Villa | |||||
| 2023/08/23 | Narva Trans | | 5-0 |  | Zenit Tallinn | ||||
| Tallinna FC Zapoos |  | 1-4 | | Kalev Tallinn | |||||
| 2023/08/29 | Maksatransport |  | 0-3 | | Läänemaa JK | ||||
| 2023/08/30 | Team Helm |  | 3-7 | | Kalev Tallinn B | ||||
| 2023/09/06 | Parnu JK Poseidon |  | 2-3 | | Arukula | ||||
| 2023/09/09 | Kuressaare | | 9-1 |  | FC Kose | ||||
| 2023/09/11 | Nomme Kalju | | 5-1 |  | Viljandi Tulevik | ||||
| Tallinna FC Olympic |  | 0-8 | | Harju JK | |||||
| 2023/09/13 | FC Flora B | | 13-0 |  | TJK Legion B | ||||
| 2023/09/20 | TJK Legion | | 1-3 | | JK Tammeka | ||||
| 2023/10/14 | FC Tallinn |  | 1-1 a.e.t. | | Viimsi | ||||
| 2023/10/18 | Tabasalu JK |  | 1-1 | | Paide LM | ||||
| 2023/11/25 | FC Flora | | 1-0 |  | JK Vaprus |
