| Round of 16 | ||||||||
|---|---|---|---|---|---|---|---|---|
| 14/10/2023 | 12:00 | JK Nõmme Kalju |
|
- |
|
Harju JK | 3:1 (1:0) | |
| 18/10/2023 | 17:00 | Läänemaa JK |
|
- |
|
Arukula FC Vigri | 9:1 (4:0) | |
| 18/11/2023 | 12:00 | Viimsi JK |
|
- |
|
JK Narva Trans | 1:0 (0:0) | |
| 24/11/2023 | 16:00 | Paide Linnameeskond |
|
- |
|
JK Tallinna Kalev II | 4:0 | |
| 24/11/2023 | 17:00 | FCI Levadia |
|
- |
|
JK Tammeka | 4:2 (3:1) | |
| 25/11/2023 | 10:30 | FC Kuressaare |
|
- |
|
FC Flora II | 4:2 (4:1) | |
| 26/11/2023 | 12:30 | JK Tallinna Kalev |
|
- |
|
Nõmme United | 3:1 (0:1) | |
| 03/12/2023 | 10:30 | FC Flora |
|
- |
|
FC Elva | 10:0 (4:0) | |
