1. Round
23/09/2008 14:00 Ethnikos Assias - ASIL Lysi 0:0
14:00 Ermis Aradippou - APEP Pitsilias 1:1
24/09/2008 14:00 PAEEK - Atromitos Yeroskipou 0:2
14:00 Onisilos Sotiras - ENTHOI Lakatamia 0:1
14:00 Nea Salamina - Doxa Katokopias 1:3
14:00 MEAP Nisou - AEK Larnaca 0:1
14:00 Chalkanoras Idaliou - Enosis Neon Paralimni 2:3
14:00 Aris Limassol - AE Paphos 1:1
17:00 Olympiakos Nikosia - AEL Limassol 0:3
01/10/2008 14:00 AO Agia Napa - Ethnikos Achna 2:2
14:00 Omonia Aradippou - APOP Kinyras 0:2
14:00 Dighenis Morphou - Alki Larnaca 3:3
04/10/2008 14:00 ASIL Lysi - Ethnikos Assias 0:2
14:00 Atromitos Yeroskipou - PAEEK 0:0
14:00 ENTHOI Lakatamia - Onisilos Sotiras 1:1
14:00 Doxa Katokopias - Nea Salamina 1:1
14:00 AEK Larnaca - MEAP Nisou 3:0
14:00 Enosis Neon Paralimni - Chalkanoras Idaliou 0:0
14:00 AEL Limassol - Olympiakos Nikosia 3:2
05/10/2008 14:00 APEP Pitsilias - Ermis Aradippou 2:2 aet
14:00 AE Paphos - Aris Limassol 1:0
14:00 Ethnikos Achna - AO Agia Napa 3:0
14:00 APOP Kinyras - Omonia Aradippou 1:2
17:00 Alki Larnaca - Dighenis Morphou 1:2
Round of 16
14/01/2009 13:00 Ermis Aradippou - ENTHOI Lakatamia 3:1
14:00 Omonia Nikosia - Dighenis Morphou 3:1
14:00 AEK Larnaca - APOP Kinyras 0:2
16:00 AE Paphos - AEL Limassol 0:1
21/01/2009 13:00 Ethnikos Assias - Ethnikos Achna 1:5
14:00 APOEL Nikosia - Doxa Katokopias 2:2
15:00 Atromitos Yeroskipou - Enosis Neon Paralimni 0:0
16:00 Anorthosis Famagusta - Apollon Limassol 2:1
28/01/2009 13:00 ENTHOI Lakatamia - Ermis Aradippou 1:4
14:00 Dighenis Morphou - Omonia Nikosia 1:2
15:00 APOP Kinyras - AEK Larnaca 1:1
16:00 AEL Limassol - AE Paphos 2:1
04/02/2009 13:00 Enosis Neon Paralimni - Atromitos Yeroskipou 3:0
13:00 Ethnikos Achna - Ethnikos Assias 3:1
14:00 Doxa Katokopias - APOEL Nikosia 2:3
16:00 Apollon Limassol - Anorthosis Famagusta 3:1 aet
Quarter-finals
25/02/2009 14:00 Omonia Nikosia - APOP Kinyras 0:0
16:00 Ethnikos Achna - AEL Limassol 1:1
04/03/2009 14:00 Ermis Aradippou - APOEL Nikosia 1:1
16:00 Apollon Limassol - Enosis Neon Paralimni 2:1
11/03/2009 14:00 APOP Kinyras - Omonia Nikosia 3:0
16:00 AEL Limassol - Ethnikos Achna 2:0
18/03/2009 14:00 APOEL Nikosia - Ermis Aradippou 3:0
16:00 Enosis Neon Paralimni - Apollon Limassol 3:2
Semi-finals
15/04/2009 15:00 Apollon Limassol - AEL Limassol 1:1
17:00 APOP Kinyras - APOEL Nikosia 2:0
06/05/2009 16:00 AEL Limassol - Apollon Limassol 2:1 aet
17:30 APOEL Nikosia - APOP Kinyras 1:0
Final
16/05/2009 17:30 APOP Kinyras - AEL Limassol 2:0
Kypello Kyprou
Kypello Kyprou

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