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| H | Olympiakos Nikosia | - | Doxa Katokopias | 1:3 | ||
| R | Doxa Katokopias | - | Olympiakos Nikosia | 6:0 | ||
| H: 08.01.2014 13:30 | R: 15.01.2014 12:30 | Sieger: Doxa Katokopias | ||||
| H | AE Kouklion | - | Ermis Aradippou | 1:0 | ||
| R | Ermis Aradippou | - | AE Kouklion | 0:1 | ||
| H: 08.01.2014 14:00 | R: 15.01.2014 16:00 | Sieger: AE Kouklion | ||||
| H | Enosis Neon Paralimni | - | Ethnikos Achna | 0:0 | ||
| R | Ethnikos Achna | - | Enosis Neon Paralimni | 1:1 | ||
| H: 08.01.2014 16:00 | R: 29.01.2014 14:00 | Sieger: Enosis Neon Paralimni | ||||
| H | Apollon Limassol | - | Nea Salamina | 1:0 | ||
| R | Nea Salamina | - | Apollon Limassol | 1:3 | ||
| H: 08.01.2014 17:00 | R: 22.01.2014 16:00 | Sieger: Apollon Limassol | ||||
| H | APOEL Nikosia | - | AEL Limassol | 1:0 | ||
| R | AEL Limassol | - | APOEL Nikosia | 0:1 | ||
| H: 08.01.2014 18:00 | R: 22.01.2014 14:00 | Sieger: APOEL Nikosia | ||||
| H | Omonia Nikosia | - | Aris Limassol | 1:0 | ||
| R | Aris Limassol | - | Omonia Nikosia | 1:1 | ||
| H: 15.01.2014 17:00 | R: 29.01.2014 16:00 | Sieger: Omonia Nikosia | ||||
| H | Anorthosis Famagusta | - | AEK Larnaca | 1:1 | ||
| R | AEK Larnaca | - | Anorthosis Famagusta | 3:1 | ||
| H: 15.01.2014 18:00 | R: 29.01.2014 14:00 | Sieger: AEK Larnaca | ||||
| H | Alki Larnaca | - | Onisilos Sotiras | 3:3 | ||
| R | Onisilos Sotiras | - | Alki Larnaca | 0:2 | ||
| H: 22.01.2014 14:00 | R: 29.01.2014 14:00 | Sieger: Alki Larnaca | ||||
