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