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| 1st(1st leg) | AEL Limassol | - | Ermis Aradippou | 4:0 (3:0) | ||
| 2nd (2nd leg) | Ermis Aradippou | - | AEL Limassol | 2:3 (0:2) | ||
| 1st(1st leg): 20/02/2019 14:00 | 2nd (2nd leg): 27/02/2019 14:00 | Winner: AEL Limassol | ||||
| 1st(1st leg) | Paphos FC | - | Enosis Neon Paralimni | 2:2 (1:1) | ||
| 2nd (2nd leg) | Enosis Neon Paralimni | - | Paphos FC | 1:1 (0:1) | ||
| 1st(1st leg): 20/02/2019 15:00 | 2nd (2nd leg): 27/02/2019 15:00 | Winner: Enosis Neon Paralimni | ||||
| 1st(1st leg) | APOEL Nikosia | - | AEK Larnaca | 1:1 (1:1) | ||
| 2nd (2nd leg) | AEK Larnaca | - | APOEL Nikosia | 3:3 (1:1) | ||
| 1st(1st leg): 27/02/2019 16:00 | 2nd (2nd leg): 06/03/2019 16:00 | Winner: APOEL Nikosia | ||||
| 1st(1st leg) | Karmiotissa Polemidion | - | Apollon Limassol | 1:5 (1:4) | ||
| 2nd (2nd leg) | Apollon Limassol | - | Karmiotissa Polemidion | 2:1 (2:0) | ||
| 1st(1st leg): 27/02/2019 17:00 | 2nd (2nd leg): 06/03/2019 15:00 | Winner: Apollon Limassol | ||||
