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| 20/08/2019 | 10:00 | FC Tarvastu | - | FC Elva | 1:4 | |
| 10:00 | Põhja-Sakala | - | JK Tallinna Kalev | 0:3 | ||
| 24/08/2019 | 12:00 | SC ReUnited | - | FC Npm Silmet | 5:2 | |
| 27/08/2019 | 18:15 | Rasmus Värki Jalgpallikool | - | Anija United | 3:0 | |
| 04/09/2019 | 16:00 | Paide Linnameeskond | - | Põhja-Tallinna JK Volta | 13:0 | |
| 17:00 | Tulevik Viljandi | - | Tallinna Wolves | 11:0 | ||
| 17:15 | Tallinna JK Legion II | - | JK Tammeka | 0:1 | ||
| 05/09/2019 | 19:00 | Põhja-Tallinna JK Volta II | - | Viimsi JK | 2:0 | |
| 07/09/2019 | 14:00 | Team Helm JK | - | FCI Levadia | 1:21 | |
| 14:00 | Võru FC Helios | - | Tartu JK Welco | 2:1 | ||
| 11/09/2019 | 17:00 | Kohtla-Järve JK Järve II | - | JK Tallinna Kalev III | 10:9 pso | |
| 25/09/2019 | 15:00 | FC Kuressaare | - | JK Narva Trans | 1:3 | |
| 09/10/2019 | 18:30 | Eston Villa II | - | FC Otepää | 3:0 | |
| 12/10/2019 | 11:00 | Paide Linnameeskond III | - | JK Nõmme Kalju | 0:3 aet | |
| 23/10/2019 | 17:00 | Maardu Linnameeskond | - | FC Flora | 0:7 | |
| 29/10/2019 | 17:00 | Tabasalu JK | - | FC Flora II | 2:1 |
