1. Round
30/10/2019 12:30 Olympiakos Nikosia - P.O. Xylotymbou 5:3 (4:1)
12:30 Onisilos Sotiras - Ethnikos Achna 1:5 (0:0)
27/11/2019 12:30 AO Agia Napa - Paphos FC 0:3 (0:0)
04/12/2019 12:30 Othellos Athienou - Enosis Neon Paralimni 2:3 (0:0)
12:30 Akritas Chlorakas - Doxa Katokopias 0:7 (0:3)
12:30 Apollon Limassol - Aris Limassol 5:1 (0:0)
Round of 16
08/01/2020 14:30 AEK Larnaca - Karmiotissa Polemidion 3:0 (0:0)
15:00 Enosis Neon Paralimni - Doxa Katokopias 0:2 (0:1)
17:00 Alki Oroklini - AEL Limassol 1:5 (1:2)
15/01/2020 14:00 Paphos FC - Nea Salamina 0:1 (0:1)
15:00 Olympiakos Nikosia - Anorthosis Famagusta 0:0 (0:0)
17:00 Ermis Aradippou - Omonia Nikosia 0:5 (0:3)
22/01/2020 17:00 Apollon Limassol - APOEL Nikosia 1:0 (1:0)
29/01/2020 12:30 Dighenis Morphou - Ethnikos Achna 0:3 (0:1)
15/01/2020 14:00 AEL Limassol - Alki Oroklini 2:1 (0:1)
22/01/2020 14:00 Omonia Nikosia - Ermis Aradippou 3:0 (2:0)
15:00 Doxa Katokopias - Enosis Neon Paralimni 1:1 (0:0)
16:00 Karmiotissa Polemidion - AEK Larnaca 0:1 (0:0)
29/01/2020 14:30 Nea Salamina - Paphos FC 2:1 (1:1)
14:30 APOEL Nikosia - Apollon Limassol 1:2 (0:1)
17:00 Anorthosis Famagusta - Olympiakos Nikosia 3:0 (2:0)
05/02/2020 12:30 Ethnikos Achna - Dighenis Morphou 3:0 (1:0)
Quarter-finals
06/02/2020 15:00 Omonia Nikosia - Doxa Katokopias 4:1 (2:0)
12/02/2020 16:00 AEL Limassol - AEK Larnaca 0:0 (0:0)
19/02/2020 14:30 Anorthosis Famagusta - Nea Salamina 1:1 (0:0)
15:00 Apollon Limassol - Ethnikos Achna 2:0 (1:0)
17:00 Doxa Katokopias - Omonia Nikosia 1:1 (0:1)
17:00 AEK Larnaca - AEL Limassol 1:1 (1:1)
26/02/2020 15:00 Nea Salamina - Anorthosis Famagusta 0:2 (0:1)
17:00 Ethnikos Achna - Apollon Limassol 2:1 (1:0, 2:0) aet
Semi-finals
22/04/2020 Apollon Limassol - AEL Limassol dnp
Omonia Nikosia - Anorthosis Famagusta dnp
29/04/2020 AEL Limassol - Apollon Limassol dnp
Anorthosis Famagusta - Omonia Nikosia dnp
Kypello Kyprou
Kypello Kyprou

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