Anorthosis FC 2-3 EN Paralimni *
| 23.01.2019 | EN Paralimni | 0-0 | Anorthosis FC | |
| 16.01.2019 | Anorthosis FC | 2-3 | EN Paralimni | |
*APOEL FC 5-1 Doxa Katokopia
| 20.02.2019 | Doxa Katokopia | 0-3 | APOEL FC | |
| 02.01.2019 | APOEL FC | 2-1 | Doxa Katokopia | |
*Ermis Aradippou 7-0 ASIL Lysi
| 16.01.2019 | ASIL Lysi | 0-4 | Ermis Aradippou | |
| 02.01.2019 | Ermis Aradippou | 3-0 | ASIL Lysi | |
*AEL Limassol 14-0 EN THOI Lakatamia
| 13.02.2019 | EN THOI Lakatamia | 0-6 | AEL Limassol | |
| 30.01.2019 | AEL Limassol | 8-0 | EN THOI Lakatamia | |
*Karmiotissa Polemidion 5-2 Ethnikos Achnas
| 20.02.2019 | Ethnikos Achnas | 1-3 | Karmiotissa Polemidion | |
| 23.01.2019 | Karmiotissa Polemidion | 2-1 | Ethnikos Achnas | |
Nea Salamina 1-4 AEK Larnaca *
| 30.01.2019 | AEK Larnaca | 2-0 | Nea Salamina | |
| 16.01.2019 | Nea Salamina | 1-2 | AEK Larnaca | |
*Apollon Limassol 2-1 Omonia Nicosia
| 16.01.2019 | Omonia Nicosia | 1-1 | Apollon Limassol | |
| 02.01.2019 | Apollon Limassol | 1-0 | Omonia Nicosia | |
Aris Limassol 3-5 Pafos FC *
| 23.01.2019 | Pafos FC | 4-1 | Aris Limassol | |
| 16.01.2019 | Aris Limassol | 2-1 | Pafos FC | |