| ROUND | R3 | R4 | QF | SF | F |
| Season archive |
| Thursday, 10 September 2020 | ||||||
| r3 | Raplamaa | 1-1 | Tallinna FC Hell Hunt | aet, p2-4 | ||
| 49 | 89 | |||||
| Wednesday, 16 September 2020 | ||||||
| r3 | FC Kose | 0-8 | Tulevik Viljandi | |||
| 15(p) | Riiberg | |||||
| 17 | Komissarov | |||||
| 28 | Peips | |||||
| 38 | Riiberg | |||||
| 43 | Peips | |||||
| 60 | Marin | |||||
| 63 | Seeder | |||||
| 77 | Marin | |||||
| Wednesday, 23 September 2020 | ||||||
| r3 | Levadia Tallinn | 5-0 | Lilleküla JK Retro | |||
| 17 | Manucho | |||||
| 21 | Manucho | |||||
| 31 | Komlov | |||||
| 77 | Kirss | |||||
| 89 | Vaštšuk | |||||
| Tuesday, 29 September 2020 | ||||||
| r3 | Maardu Linnameeskond | 5-3 | Keila JK | |||
| 3 | Aristov | 14 | Suur | |||
| 42 | Jaagumets | 26 | ||||
| 61 | Tsõmbaljuk | 89 | Epner | |||
| 65(p) | Gussev | |||||
| 88 | Lebedev | |||||
| r3 | Tartu JK Welco | 1-6 | Kuressaare | |||
| 74(p) | Mark | 5 | Kriisa | |||
| 33 | Kelder | |||||
| 57 | Männilaan | |||||
| 61 | Männilaan | |||||
| 68 | Rass | |||||
| 85 | Männilaan | |||||
| r3 | Märjamaa Kompanii | 2-1 | Rumori Calcio II Tallinn | |||
| 52 | 2 | |||||
| 74 | ||||||
| r3 | Imavere | 0-3 | Tallinna Kalev | |||
| 10 | Reimaa | |||||
| 54 | Kaljumäe | |||||
| 68 | Velijev | |||||
| Wednesday, 30 September 2020 | ||||||
| r3 | Paide Linnameeskond | 13-0 | Tallinna FC Pocarr | |||
| 8 | Lubega | |||||
| 12 | Pelt | |||||
| 25 | Kauber | |||||
| 38 | Sinilaid | |||||
| 44(p) | Aer | |||||
| 45 | Sinilaid | |||||
| 50 | Saliste | |||||
| 61 | Palumets | |||||
| 64 | Palumets | |||||
| 66 | Aer | |||||
| 67 | Lubega | |||||
| 77 | Lubega | |||||
| 87 | Kauber | |||||
| r3 | TJK Legion | 11-0 | Saku Sporting | |||
| 18 | Gviniashvili | |||||
| 19 | Šatov | |||||
| 31 | Šatov | |||||
| 41 | Šatov | |||||
| 47 | Prosa | |||||
| 57 | Prosa | |||||
| 64 | Prosa | |||||
| 66 | Šatov | |||||
| 71 | Gussev | |||||
| 72 | Šatov | |||||
| 79 | Šatov | |||||
| r3 | Team Helm | 1-2 | Trans Narva | |||
| 49 | 32 | Sobtšenko | ||||
| 35 | Zakarlyuka | |||||
| r3 | FC Tallinn | 2-0 | Vändra Vaprus | |||
| 66(p) | Malov | |||||
| 90 | Badjuk | |||||
| Thursday, 8 October 2020 | ||||||
| r3 | Pärnu | 0-1 | Tartu Tammeka | |||
| 29 | Koskor | |||||
| Tuesday, 13 October 2020 | ||||||
| r3 | Nõmme Kalju | 4-0 | Tallinna JK Piraaja | |||
| 24 | Puri | |||||
| 34 | Subbotin | |||||
| 45 | Usta | |||||
| 70 | Puri | |||||
| Wednesday, 14 October 2020 | ||||||
| r3 | Tallinna FC Eston Villa | 1-1 | Põhja-Tallinna JK Volta | aet, p4-3 | ||
| 11(og) | Bolgov | 78 | ||||
| Wednesday, 21 October 2020 | ||||||
| r3 | JK Pärnu Sadam | - | Ida-Virumaa FC Alliance | |||
| Match awarded to Ida-Virumaa FC Alliance. | ||||||
| Thursday, 12 November 2020 | ||||||
| r3 | Põhja-Sakala | - | Flora | |||
| Match awarded to Flora. | ||||||
| 6 | +6 | Marek ŠATOV (TJK Legion) |
| 3 | +3 | Edrisa LUBEGA (Paide Linnameeskond) |
| +3 | Albert PROSA (TJK Legion) | |
| +3 | Mattias MÄNNILAAN (Kuressaare) | |
| 2 | +2 | Sander SINILAID (Paide Linnameeskond) |
| +2 | Rainer PEIPS (Tulevik Viljandi) | |
| +2 | MANUCHO (Levadia Tallinn) | |
| +2 | Herol RIIBERG (Tulevik Viljandi, 1p) | |
| +2 | Kevor PALUMETS (Paide Linnameeskond) | |
| +2 | Pavel MARIN (Tulevik Viljandi) | |
| +2 | Siim AER (Paide Linnameeskond, 1p) | |
| +2 | Sander PURI (Nõmme Kalju) | |
| +2 | Kevin KAUBER (Paide Linnameeskond) |