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| H | Donegal Celtic FC | - | Cliftonville FC | 0:1 | ||
| R | Cliftonville FC | - | Donegal Celtic FC | 2:1 | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Cliftonville FC | ||||
| H | Portadown FC | - | Crusaders FC | 2:1 | ||
| R | Crusaders FC | - | Portadown FC | 3:4 | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Portadown FC | ||||
| H | Glentoran FC | - | Glenavon FC | 2:2 | ||
| R | Glenavon FC | - | Glentoran FC | 2:3 | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Glentoran FC | ||||
| H | Institute FC Drumahoe | - | Ballymena United | 2:1 | ||
| R | Ballymena United | - | Institute FC Drumahoe | 1:2 | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Institute FC Drumahoe | ||||
| H | Newry City FC | - | Linfield FC | 1:1 | ||
| R | Linfield FC | - | Newry City FC | 0:0 | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Linfield FC | ||||
| H | Ballinamallard United FC | - | Limavady United | 0:0 | ||
| R | Limavady United | - | Ballinamallard United FC | 0:1 | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Ballinamallard United FC | ||||
| H | Lisburn Distillery | - | Coleraine FC | 1:0 | ||
| R | Coleraine FC | - | Lisburn Distillery | 5:4 i.E. | ||
| H: 31.10.2009 | R: 10.11.2009 | Sieger: Coleraine FC | ||||
