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1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2008/09
1/16-finals
| 1 | Kinyras Peyias | Omonia Aradippou | 1 : 2, 2 : 0 |
| 2 | M.E.A.P. Nisou | AEK Larnaca | 0 : 3, 0 : 1 |
| 3 | Digenis Akritas | Alki Larnaca | 2 : 1, 4 : 3 |
| 4 | Bye | Omonia | |
| 5 | Ermis | APEP | 2 : 2, 1 : 1 |
| 6 | Sotiras | Thoi Lakatamias | 1 : 1, 0 : 1 |
| 7 | Doxa | Nea Salamis | 1 : 1, 3 : 1 |
| 8 | Bye | APOEL | |
| 9 | Apollon | Bye | |
| 10 | Bye | Anorthosis | |
| 11 | Atromitos Y. | PAEEK | 3 : 1, 2 : 0 |
| 12 | Halkanoras | Paralimni | 0 : 0, 2 : 3 |
| 13 | Achnas | Ayia Napa | 3 : 0, 2 : 2 |
| 14 | ASIL Lysi | Ethn. Assias | 0 : 2, 0 : 0 |
| 15 | Paphos | Aris | 1 : 0, 1 : 1 |
| 16 | Ol. Nicosia | AEL Limassol | 2 : 3, 0 : 3 |
1/8-finals
| 1 | Kinyras Peyias | AEK Larnaca | 1 : 1, 2 : 0 |
| 2 | Digenis Akritas | Omonia | 1 : 2, 1 : 3 |
| 3 | Ermis | Thoi Lakatamias | 4 : 1, 3 : 1 |
| 4 | Doxa | APOEL | 2 : 3, 2 : 2 |
| 5 | Apollon | Anorthosis | 3 : 1, 1 : 2 |
| 6 | Atromitos Y. | Paralimni | 0 : 3, 0 : 0 |
| 7 | Achnas | Ethn. Assias | 3 : 1, 5 : 1 |
| 8 | Paphos | AEL Limassol | 1 : 2, 0 : 1 |
Quarter-finals
| 1 | Kinyras Peyias | Omonia | 3 : 0, 0 : 0 |
| 2 | Ermis | APOEL | 0 : 3, 1 : 1 |
| 3 | Apollon | Paralimni | 2 : 3, 2 : 1 |
| 4 | Achnas | AEL Limassol | 0 : 2, 1 : 1 |
Semi-finals
| 1 | Kinyras Peyias | APOEL | 0 : 1, 2 : 0 |
| 2 | Apollon | AEL Limassol | 1 : 2, 1 : 1 |
Final
| 1 | Kinyras Peyias | AEL Limassol | 2 : 0 |
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