Winner
| 1/4 | 1/2 | Final |
|---|---|---|
| FC Spartak Tallinn | ||
13.01.2024  0 - 7  Tallinna Humanitaargümnaasium | ||
| FC Scandinor | ||
10.02.2024 1 - 4  Tallinna Humanitaargümnaasium | ||
| FC Scandinor | ||
| TMJK | ||
| FC Merivälja | 21.02.2024 6 - 2  Tallinna Humanitaargümnaasium | |
06.01.2024  1 - 6 Tallinna Humanitaargümnaasium | ||
| TMJK | ||
| TMJK | ||
| Atlantic FC | ||
06.01.2024  6 - 4  Tallinna Humanitaargümnaasium | ||
| Atlantic FC | ||
10.02.2024 0 - 4 Tallinna Humanitaargümnaasium | ||
| Eyjafjallajökull | ||
| FC Smsraha | ||
| Maccabi | ||
13.01.2024  1 - 5 Tallinna Humanitaargümnaasium | ||
| FC Smsraha | ||
| FC Smsraha |
Groups
Grandliiga Cup 2023/24 (A)
| Club | Played | W | D | L | GF | GA | +/- | Points | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |  Maardu LM | 3 | 3 | 0 | 0 | 23 | 5 | 18 | 9 |
| 2 |  FC Doker | 3 | 2 | 0 | 1 | 23 | 10 | 13 | 6 |
| 3 |  Atlantic FC | 3 | 1 | 0 | 2 | 8 | 15 | -7 | 3 |
| 4 |  FC Spartak Tallinn | 3 | 0 | 0 | 3 | 5 | 29 | -24 | 0 |
Grandliiga Cup 2023/24 (B)
| Club | Played | W | D | L | GF | GA | +/- | Points | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |  Kopli City | 3 | 3 | 0 | 0 | 20 | 4 | 16 | 9 |
| 2 |  FC Victoria | 3 | 2 | 0 | 1 | 12 | 10 | 2 | 6 |
| 3 |  FC Scandinor | 3 | 0 | 1 | 2 | 6 | 12 | -6 | 1 |
| 4 |  Eyjafjallajökull | 3 | 0 | 1 | 2 | 5 | 17 | -12 | 1 |
Grandliiga Cup 2023/24 (C)
| Club | Played | W | D | L | GF | GA | +/- | Points | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |  FC Centurion | 3 | 3 | 0 | 0 | 13 | 5 | 8 | 9 |
| 2 |  O.Z. Company | 3 | 1 | 1 | 1 | 10 | 9 | 1 | 4 |
| 3 |  Maccabi | 3 | 1 | 1 | 1 | 8 | 11 | -3 | 4 |
| 4 |  FC Merivälja | 3 | 0 | 0 | 3 | 3 | 9 | -6 | 0 |
Grandliiga Cup 2023/24 (D)
| Club | Played | W | D | L | GF | GA | +/- | Points | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |  Tallinn Shipyard | 3 | 3 | 0 | 0 | 23 | 3 | 20 | 9 |
| 2 |  FCS Loo | 3 | 2 | 0 | 1 | 9 | 13 | -4 | 6 |
| 3 | TMJK | 3 | 1 | 0 | 2 | 11 | 14 | -3 | 3 |
| 4 |  FC Smsraha | 3 | 0 | 0 | 3 | 9 | 22 | -13 | 0 |