Results| Wednesday, 16 August 2023 |
| r3 | FA Tartu Kalev | 2-6 | Levadia Tallinn |
|
| 8(p) | Peedo |
| 14 | Felipe Felício |
|
| 52 | |
| 37 | Felipe Felício |
|
| |
| 47 | Kirss |
|
| |
| 69 | Roosnupp |
|
| |
| 73 | Felipe Felício |
|
| |
| 90+1 | Käblik |
|
| Tuesday, 22 August 2023 |
| r3 | Elva | 5-2 | Pärnu JK Tervis |
|
| 51 | Härm |
| 13 | Saarts |
|
| 61 | Härm |
| 73 | Hanson |
|
| 66 | Paju |
| |
|
| 78 | Kütt |
| |
|
| 84 | Kuresoo |
| |
|
| r3 | Nõmme United | 11-1 | Tallinna FC Eston Villa |
|
| 10 | Riisenberg |
| 12 | Preiman |
|
| 17 | Riisenberg |
| |
|
| 20 | Alteberg |
| |
|
| 38 | Valge |
| |
|
| 41 | Alteberg |
| |
|
| 47 | Leoke |
| |
|
| 54 | Riisenberg |
| |
|
| 75 | Leoke |
| |
|
| 81 | Riisenberg |
| |
|
| 88 | Vendelin |
| |
|
| 90+1 | Leoke |
| |
|
| Wednesday, 23 August 2023 |
| r3 | Trans Narva | 5-0 | FC Zenit Tallinn |
|
| 10 | Volkov |
| |
|
| 27 | Suárez |
| |
|
| 53 | Volkov |
| |
|
| 72 | Koskor |
| |
|
| 75 | Kulinitš |
| |
|
| r3 | Tallinna FC Zapoos | 1-4 | Tallinna Kalev |
|
| 19 | |
| 8 | Kiivit |
|
| |
| 16(og) | |
|
| |
| 22 | Smirnov |
|
| |
| 27 | Trawally |
|
| Tuesday, 29 August 2023 |
| r3 | Maksatransport | 0-3 | Läänemaa JK |
|
| |
| 45 | Siim |
|
| |
| 85 | Veski |
|
| |
| 90+3 | Konks |
|
| Wednesday, 30 August 2023 |
| r3 | Team Helm | 3-7 | Tallinna Kalev II |
|
| 47 | Litvjakov |
| 28 | Luik |
|
| 54 | Läll |
| 36 | Luik |
|
| 70 | Läll |
| 45 | Luik |
|
| |
| 56 | Sandre |
|
| |
| 79 | Laasner |
|
| |
| 83 | Roots |
|
| |
| 84 | Kippar |
|
| Wednesday, 6 September 2023 |
| r3 | Pärnu JK Poseidon | 2-3 | Aruküla FC Vigri | aet |
| 56 | Pulst |
| 60 | Randjõe |
|
| 118 | Tammsaar |
| 102 | Mere |
|
| |
| 107 | Kutser |
|
| Saturday, 9 September 2023 |
| r3 | Kuressaare | 9-1 | FC Kose |
|
| 2 | Suursaar |
| 83 | Eerits |
|
| 11 | Kivi |
| |
|
| 22 | Suursaar |
| |
|
| 38 | Kobin |
| |
|
| 40 | Leedo |
| |
|
| 45+2(p) | Kivi |
| |
|
| 62(p) | Kivi |
| |
|
| 76 | Suursaar |
| |
|
| 84 | Metsmaa |
| |
|
| Monday, 11 September 2023 |
| r3 | Nõmme Kalju | 5-1 | Tulevik Viljandi |
|
| 5(p) | Rommens |
| 15(og) | Avilov |
|
| 37 | David |
| |
|
| 67 | David |
| |
|
| 78 | Siht |
| |
|
| 82 | David |
| |
|
| r3 | FC Olympic | 0-8 | Harju JK Laagri |
|
| |
| 12 | Järva |
|
| |
| 25 | Usta |
|
| |
| 38 | Usta |
|
| |
| 41 | Rudenko |
|
| |
| 55 | Reimaa |
|
| |
| 63 | Reimaa |
|
| |
| 73 | Rudenko |
|
| |
| 74 | Kose |
|
| Wednesday, 13 September 2023 |
| r3 | Flora II | 13-0 | TJK Legion II |
|
| 4 | Palts |
| |
|
| 13 | Randväli |
| |
|
| 35 | Valdaru |
| |
|
| 39 | Grün |
| |
|
| 45+1 | Piil |
| |
|
| 48 | Dyakiv |
| |
|
| 49 | Lukas |
| |
|
| 61 | Lukas |
| |
|
| 63 | Palts |
| |
|
| 69 | Eenmaa |
| |
|
| 74 | Randväli |
| |
|
| 79 | Lukas |
| |
|
| 89 | Vain |
| |
|
| Wednesday, 20 September 2023 |
| r3 | TJK Legion | 1-3 | Tartu Tammeka |
|
| 22 | Ruus |
| 61 | Veelma |
|
| |
| 90 | Mätas |
|
| |
| 90+3 | Adebayo |
|
| Saturday, 14 October 2023 |
| r3 | FC Tallinn | 1-1 | Viimsi JK | aet, p5-6 |
| 51 | Šišov |
| 44 | Krimm |
|
| Wednesday, 18 October 2023 |
| r3 | JK Tabasalu | 1-3 | Paide Linnameeskond | aet |
| 84 | Nahk |
| 67 | Agyepong |
|
| |
| 103 | Saag |
|
| |
| 114 | Saag |
|
| Saturday, 25 November 2023 |
| r3 | Flora | 1-0 | Pärnu |
|
| 27 | Mihhailov |
| |
|
Eesti Karikas
