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| 26.03.2014 | ||||
| 01:35 | CFUCC Group 3 | Harbour View | 0-2 | Defence Force |
| 01:00 | CFUCC Group 1 | Bayamón FC | 1-1 | USR Sainte-Rose |
| 25.03.2014 | ||||
| 23:00 | CFUCC Group 2 | AS Mirebalais | 2-1 | Inter Moengotapoe |
| 22:00 | CFUCC Group 1 | Bodden Town | 2-4 | RKSV Centro Dominguito |
| 21:00 | CFUCC Group 2 | Morvant Caledonia Utd | 0-4 | Waterhouse FC |
| 24.03.2014 | ||||
| 01:30 | CFUCC Group 3 | Harbour View | 0-1 | Alpha United |
| 23.03.2014 | ||||
| 23:00 | CFUCC Group 2 | AS Mirebalais | 1-2 | Waterhouse FC |
| 23:00 | CFUCC Group 1 | Bayamón FC | 0-0 | RKSV Centro Dominguito |
| 21:00 | CFUCC Group 2 | Inter Moengotapoe | 2-2 | Morvant Caledonia Utd |
| 20:30 | CFUCC Group 1 | USR Sainte-Rose | 1-0 | Bodden Town |
| 22.03.2014 | ||||
| 01:35 | CFUCC Group 3 | Alpha United | 2-0 | Defence Force |
| 01:00 | CFUCC Group 1 | Bayamón FC | 5-0 | Bodden Town |
| 00:00 | CFUCC Group 2 | AS Mirebalais | 0-3 | Morvant Caledonia Utd |
| 21.03.2014 | ||||
| 22:00 | CFUCC Group 1 | RKSV Centro Dominguito | 0-0 | USR Sainte-Rose |
| 22:00 | CFUCC Group 2 | Waterhouse FC | 4-0 | Inter Moengotapoe |