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| 25/09/2019 | 17:00 | SC ReUnited | - | Kohtla-Järve JK Järve II | 1:2 | |
| 13/10/2019 | 11:00 | Rasmus Värki Jalgpallikool | - | Võru FC Helios | 0:1 | |
| 22/10/2019 | 17:00 | JK Narva Trans | - | Eston Villa II | 21:0 | |
| 23/10/2019 | 17:00 | JK Tallinna Kalev | - | Põhja-Tallinna JK Volta II | 7:0 | |
| 18:30 | FCI Levadia | - | JK Nõmme Kalju | 1:2 | ||
| 30/10/2019 | 17:00 | Tulevik Viljandi | - | JK Tammeka | 0:1 | |
| 17:00 | Paide Linnameeskond | - | FC Flora | 1:3 | ||
| 06/11/2019 | 17:00 | FC Elva | - | Tabasalu JK | 2:0 |
