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1/64-finals
1/32-finals
1/16-finals
2026/27
1/64-finals
| 1 | Narva | Vana Hea Puur | 10 : 0 |
| 2 | Bye | Flora U21 | |
| 3 | Marjamaa Kompanii | Bye | |
| 4 | Bye | Generation Tallinn | |
| 5 | TalTech | Bye | |
| 6 | Bye | Keila JK | |
| 7 | Flora U19 | Bye | |
| 8 | Bye | Pohja-Tallinna JK Volta | |
| 9 | EstHam United | Bye | |
| 10 | Kose | Kummik | 8 : 0 |
| 11 | Rumori Calcio II | Bye | |
| 12 | Bye | Tartu Welco | |
| 13 | Harju JK Laagri | Bye | |
| 14 | Bye | Rae Spordikool | |
| 15 | Tallinna Wolves | Tabasalu | 0 : 10 |
| 16 | Bye | Tamper | |
| 17 | Levadia | Bye | |
| 20 | Bye | Paide | |
| 21 | Johvi Phoenix | Elva III | 4 : 2 |
| 22 | Bye | Hell Hunt | |
| 23 | Lahte United | Tabasalu Ulasabat | 1 : 3 |
| 24 | Bye | Parnu JK Vaprus | |
| 25 | Hiiumaa | Bye | |
| 26 | Bye | Tulevik | |
| 27 | Nomme Utd | Bye | |
| 28 | Bye | Raplamaa | |
| 29 | Tartu Helios | Bye | |
| 30 | Bye | Soccernet | |
| 31 | Viimsi JK | Bye | |
| 32 | Bye | Nomme Utd U19 | |
| 33 | Flora | Bye | |
| 35 | JK Arsenal | Tallinna Kalev U21 | 0 : 3 |
| 36 | Rakvere FC Freedom | Kena | 3 : 2 |
| 37 | Haapsalu | Bye | |
| 38 | Jarva-Jaani | Elva | 0 : 4 |
| 39 | Arukula Vigri | Bye | |
| 40 | Bye | Raasiku Joker | |
| 41 | TransferWise | Bye | |
| 42 | Bye | Olympic Tallinn | |
| 43 | Saku Sporting | Bye | |
| 44 | Bye | Legion | |
| 45 | Kohvile | Bye | |
| 46 | Bye | Rumori Calcio | |
| 47 | Tammeka | Bye | |
| 48 | Bye | Zealot Sporting | |
| 49 | Kristiine | Bye | |
| 50 | Bye | Jogeva Wolves | |
| 51 | Kuressaare | Bye | |
| 52 | Bye | Tartu Welco 2 | |
| 53 | JK Poseidon | Bye | |
| 54 | Helm | Deliirium | 30 : 0 |
| 56 | Bye | Kalju | |
| 57 | FC Tallinn | Bye | |
| 58 | Bye | Tallinna FC Zapoos | |
| 59 | Saue Laagri | Viimsi Lovid | 6 : 0 |
| 60 | Bye | Harju JK Laagri U21 | |
| 61 | Tammeka Tartu U19 | Bye | |
| 62 | Bye | Tallinna Kalev | |
| 63 | Tartu Kalev | Paide III | 4 : 3 |
| 64 | Bye | Kuusalu Kalev |
1/32-finals
| 1 | Narva | Flora U21 | 1 : 0 |
| 2 | Marjamaa Kompanii | Generation Tallinn | 8 : 4 |
| 3 | TalTech | Keila JK | 0 : 6 |
| 4 | Flora U19 | Pohja-Tallinna JK Volta | |
| 5 | EstHam United | Kose | 1 : 5 |
| 6 | Rumori Calcio II | Tartu Welco | 0 : 12 |
| 7 | Harju JK Laagri | Rae Spordikool | 8 : 0 |
| 8 | Tabasalu | Tamper | 0 : 2 |
| 9 | Levadia | Bye | |
| 10 | Bye | Paide | |
| 11 | Johvi Phoenix | Hell Hunt | 8 : 1 |
| 12 | Tabasalu Ulasabat | Parnu JK Vaprus | 1 : 4 |
| 13 | Hiiumaa | Tulevik | 4 : 1 |
| 14 | Nomme Utd | Raplamaa | 12 : 0 |
| 15 | Tartu Helios (WO.) | Soccernet | |
| 16 | Viimsi JK | Nomme Utd U19 | 4 : 0 |
| 17 | Flora | Bye | |
| 18 | Tallinna Kalev U21 | Rakvere FC Freedom | 4 : 2 |
| 19 | Haapsalu | Elva | 0 : 6 |
| 20 | Arukula Vigri | Raasiku Joker | 0 : 1 |
| 21 | TransferWise | Olympic Tallinn | 3 : 6 |
| 22 | Saku Sporting | Legion | 2 : 1 |
| 23 | Kohvile | Rumori Calcio | 1 : 4 |
| 24 | Tammeka | Zealot Sporting | 19 : 0 |
| 25 | Kristiine | Jogeva Wolves | 8 : 3 |
| 26 | Kuressaare | Tartu Welco 2 | 5 : 1 |
| 27 | JK Poseidon | Helm | 3 : 2 |
| 28 | Bye | Kalju | |
| 29 | FC Tallinn | Tallinna FC Zapoos | |
| 30 | Saue Laagri | Harju JK Laagri U21 | |
| 31 | Tammeka Tartu U19 | Tallinna Kalev | 0 : 8 |
| 32 | Tartu Kalev | Kuusalu Kalev | 7 : 0 |
1/16-finals
| 1 | Narva | Marjamaa Kompanii | |
| 2 | Keila JK | TBD #4 | |
| 3 | Kose | Tartu Welco | |
| 4 | Harju JK Laagri | Tamper | |
| 5 | Levadia | Paide | |
| 6 | Johvi Phoenix | Parnu JK Vaprus | |
| 7 | Hiiumaa | Nomme Utd | |
| 8 | Tartu Helios | Viimsi JK | |
| 9 | Flora | Tallinna Kalev U21 | |
| 10 | Elva | Raasiku Joker | |
| 11 | Olympic Tallinn | Saku Sporting | |
| 12 | Rumori Calcio | Tammeka | |
| 13 | Kristiine | Kuressaare | |
| 14 | JK Poseidon | Kalju | |
| 15 | TBD #29 | TBD #30 | |
| 16 | Tallinna Kalev | Tartu Kalev |
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