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| 1st(1st leg) | Donegal Celtic FC | - | Cliftonville FC | 0:1 | ||
| 2nd (2nd leg) | Cliftonville FC | - | Donegal Celtic FC | 2:1 | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Cliftonville FC | ||||
| 1st(1st leg) | Portadown FC | - | Crusaders FC | 2:1 | ||
| 2nd (2nd leg) | Crusaders FC | - | Portadown FC | 3:4 | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Portadown FC | ||||
| 1st(1st leg) | Glentoran FC | - | Glenavon FC | 2:2 | ||
| 2nd (2nd leg) | Glenavon FC | - | Glentoran FC | 2:3 | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Glentoran FC | ||||
| 1st(1st leg) | Institute FC Drumahoe | - | Ballymena United | 2:1 | ||
| 2nd (2nd leg) | Ballymena United | - | Institute FC Drumahoe | 1:2 | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Institute FC Drumahoe | ||||
| 1st(1st leg) | Newry City FC | - | Linfield FC | 1:1 | ||
| 2nd (2nd leg) | Linfield FC | - | Newry City FC | 0:0 | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Linfield FC | ||||
| 1st(1st leg) | Ballinamallard United FC | - | Limavady United | 0:0 | ||
| 2nd (2nd leg) | Limavady United | - | Ballinamallard United FC | 0:1 | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Ballinamallard United FC | ||||
| 1st(1st leg) | Lisburn Distillery | - | Coleraine FC | 1:0 | ||
| 2nd (2nd leg) | Coleraine FC | - | Lisburn Distillery | 5:4 pso | ||
| 1st(1st leg): 31/10/2009 | 2nd (2nd leg): 10/11/2009 | Winner: Coleraine FC | ||||
