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| 04.08.2021 | 17:00 | Tulevik Viljandi | - | Tulevik Viljandi II | 10:0 | |
| 18:00 | Paide Linnameeskond III | - | Kristiine JK | 5:0 | ||
| 09.08.2021 | JK Narva Trans | - | Eston Villa | 3:0 Wert. | ||
| 16.08.2021 | 17:00 | FC Elva | - | Viimsi JK | 2:0 | |
| 17.08.2021 | 18:00 | Läänemaa JK | - | Tallinna JK Legion | 2:8 | |
| 18.08.2021 | 18:00 | JK Nõmme Kalju | - | Tallinna FC Zapoos | 9:1 | |
| 19:00 | JK Tammeka | - | FC Kuressaare | 3:1 | ||
| 23.08.2021 | 17:30 | Raplamaa JK | - | FCI Levadia | 0:5 | |
| 25.08.2021 | 19:00 | FC Ararat TTÜ | - | FC Vastseliina | 2:3 | |
| 01.09.2021 | 18:00 | FC Helios | - | Tartu JK Welco | 0:3 | |
| 02.09.2021 | 18:00 | JK Tallinna Kalev | - | Tabasalu JK II | 3:0 | |
| 21.09.2021 | 16:00 | FA Tartu Kalev | - | Nõmme United | 4:2 | |
| 19:00 | FCI Tallinn | - | FC Flora II | 2:3 | ||
| 22.09.2021 | 19:30 | FC Tallinn | - | Paide Linnameeskond | 1:4 | |
| 06.10.2021 | 18:00 | Pärnu JK | - | Tabasalu JK | 0:1 (0:1) | |
| 12.12.2021 | 12:00 | FC Flora III | - | FC Flora | 0:14 |
