*AEK Larnaca 4-0 Karmiotissa Polemidion
| 22.01.2020 | Karmiotissa Polemidion | 0-1 | AEK Larnaca | |
| 08.01.2020 | AEK Larnaca | 3-0 | Karmiotissa Polemidion | |
Alki Oroklini 2-7 AEL Limassol
| 15.01.2020 | AEL Limassol | 2-1 | Alki Oroklini | |
| 08.01.2020 | Alki Oroklini | 1-5 | AEL Limassol | |
Olympiakos Nicosia 0-3 Anorthosis FC *
| 29.01.2020 | Anorthosis FC | 3-0 | Olympiakos Nicosia | |
| 15.01.2020 | Olympiakos Nicosia | 0-0 | Anorthosis FC | |
*Apollon Limassol 3-1 APOEL FC
| 29.01.2020 | APOEL FC | 1-2 | Apollon Limassol | |
| 22.01.2020 | Apollon Limassol | 1-0 | APOEL FC | |
Digenis Morfou 0-6 Ethnikos Achnas *
| 05.02.2020 | Ethnikos Achnas | 3-0 | Digenis Morfou | |
| 29.01.2020 | Digenis Morfou | 0-3 | Ethnikos Achnas | |
EN Paralimni 1-3 Doxa Katokopia *
| 22.01.2020 | Doxa Katokopia | 1-1 | EN Paralimni | |
| 08.01.2020 | EN Paralimni | 0-2 | Doxa Katokopia | |
Ermis Aradippou 0-8 Omonia Nicosia *
| 22.01.2020 | Omonia Nicosia | 3-0 | Ermis Aradippou | |
| 15.01.2020 | Ermis Aradippou | 0-5 | Omonia Nicosia | |
Pafos FC 1-3 Nea Salamina *
| 29.01.2020 | Nea Salamina | 2-1 | Pafos FC | |
| 15.01.2020 | Pafos FC | 0-1 | Nea Salamina | |