| ROUND | R3 | R4 | QF | SF | F |
| Season archive |
| Wednesday, 25 September 2019 | ||||||
| r4 | SC ReUnited | 1-2 | Ida-Virumaa FC Alliance II | |||
| 78(p) | Paal | 37 | Mossin | |||
| 81 | Volkov | |||||
| Sunday, 13 October 2019 | ||||||
| r4 | Rasmus Värki | 0-1 | Võru FC Helios | |||
| 65 | ||||||
| Tuesday, 22 October 2019 | ||||||
| r4 | Trans Narva | 21-0 | Tallinna FC Eston Villa II | |||
| 5 | McWoods | |||||
| 7 | McWoods | |||||
| 17 | Kasparavičius | |||||
| 22 | McWoods | |||||
| 23 | Kondrattsev | |||||
| 26 | Kasparavičius | |||||
| 27 | Golovljov | |||||
| 34 | Saliste | |||||
| 40 | McWoods | |||||
| 42 | Saliste | |||||
| 54 | Golovljov | |||||
| 59 | Golovljov | |||||
| 60 | Golovljov | |||||
| 62 | Golovljov | |||||
| 62 | Golovljov | |||||
| 65 | Mihhailov | |||||
| 67 | Golovljov | |||||
| 70 | Stepanov | |||||
| 72 | Golovljov | |||||
| 74 | Stepanov | |||||
| 80 | Golovljov | |||||
| Wednesday, 23 October 2019 | ||||||
| r4 | Levadia Tallinn | 1-2 | Nõmme Kalju | |||
| 62 | Peetson | 77(p) | Subbotin | |||
| 84(og) | Podholjuzin | |||||
| r4 | Tallinna Kalev | 7-0 | Põhja-Tallinna JK Volta II | |||
| 9 | Anier | |||||
| 25 | Hounkpe | |||||
| 28 | Alli | |||||
| 36 | Sõtšugov | |||||
| 59 | Alli | |||||
| 74 | Alli | |||||
| 90 | Sõtšugov | |||||
| Wednesday, 30 October 2019 | ||||||
| r4 | Tulevik Viljandi | 0-1 | Tartu Tammeka | |||
| 65 | Tekko | |||||
| r4 | Paide Linnameeskond | 1-3 | Flora | |||
| 18 | Välja | 57 | Poom | |||
| 73 | Sinyavskiy | |||||
| 77(p) | Sorga | |||||
| Wednesday, 6 November 2019 | ||||||
| r4 | Elva | 2-0 | JK Tabasalu | |||
| 53 | Lokk | |||||
| 54 | Timm | |||||
| 9 | +9 | Eduard GOLOVLJOV (Trans Narva) |
| 8 | Erik MORENO (Levadia Tallinn) | |
| 5 | Yann YAO (Paide Linnameeskond) | |
| 4 | +4 | Eric McWOODS (Trans Narva) |
| 3 | +2 | Joseph SALISTE (Trans Narva) |
| +1 | Vlasiy SINYAVSKIY (Flora) | |
| Rainer PEIPS (Tulevik Viljandi) | ||
| +1 | Erik SORGA (Flora, 1p) | |
| Bogdan VAŠTŠUK (Levadia Tallinn) | ||
| +3 | Wale ALLI (Tallinna Kalev) | |
| Mark ROOSNUPP (Levadia Tallinn) | ||
| Kaimar SAAG (Tulevik Viljandi) | ||
| 2 | +1 | Taarvo TIMM (Elva) |
| +1 | Markus POOM (Flora) | |
| Joel INDERMITTE (Rasmus Värki) | ||
| Sander SINILAID (Paide Linnameeskond) | ||
| +2 | Aleksei STEPANOV (Trans Narva) | |
| Arlet HUNT (Tulevik Viljandi) | ||
| Patrick SYLVA (Paide Linnameeskond) | ||
| Artjom KOMLOV (Levadia Tallinn) | ||
| Karl ÕIGUS (Levadia Tallinn) | ||
| Herol RIIBERG (Flora) | ||
| +2 | Daniil SÕTŠUGOV (Tallinna Kalev) | |
| Muhammed SANNEH (Paide Linnameeskond, 1p) | ||
| +1 | Timo PAAL (SC ReUnited, 1p) | |
| +2 | Julius KASPARAVIČIUS (Trans Narva) | |
| Erik UTGOF (Levadia Tallinn) | ||
| +1 | Markus LOKK (Elva) | |
| Max MATA (Nõmme Kalju) |