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| 04/08/2021 | 16:00 | Tulevik Viljandi | - | Tulevik Viljandi II | 10:0 | |
| 17:00 | Paide Linnameeskond III | - | Kristiine JK | 5:0 | ||
| 09/08/2021 | JK Narva Trans | - | Eston Villa | 3:0 dec. | ||
| 16/08/2021 | 16:00 | FC Elva | - | Viimsi JK | 2:0 | |
| 17/08/2021 | 17:00 | Läänemaa JK | - | Tallinna JK Legion | 2:8 | |
| 18/08/2021 | 17:00 | JK Nõmme Kalju | - | Tallinna FC Zapoos | 9:1 | |
| 18:00 | JK Tammeka | - | FC Kuressaare | 3:1 | ||
| 23/08/2021 | 16:30 | Raplamaa JK | - | FCI Levadia | 0:5 | |
| 25/08/2021 | 18:00 | FC Ararat TTÜ | - | FC Vastseliina | 2:3 | |
| 01/09/2021 | 17:00 | FC Helios | - | Tartu JK Welco | 0:3 | |
| 02/09/2021 | 17:00 | JK Tallinna Kalev | - | Tabasalu JK II | 3:0 | |
| 21/09/2021 | 15:00 | FA Tartu Kalev | - | Nõmme United | 4:2 | |
| 18:00 | FCI Tallinn | - | FC Flora II | 2:3 | ||
| 22/09/2021 | 18:30 | FC Tallinn | - | Paide Linnameeskond | 1:4 | |
| 06/10/2021 | 17:00 | Pärnu JK | - | Tabasalu JK | 0:1 (0:1) | |
| 12/12/2021 | 11:00 | FC Flora III | - | FC Flora | 0:14 |
