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| 1st(1st leg) | Cabinteely FC | - | Drogheda United | 1:1 (1:0) | ||
| 2nd (2nd leg) | Drogheda United | - | Cabinteely FC | 5:1 (1:0) | ||
| 1st(1st leg): 18/10/2019 19:45 | 2nd (2nd leg): 25/10/2019 19:45 | Winner: Drogheda United | ||||
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| 1st(1st leg) | Cabinteely FC | - | Drogheda United | 1:1 (1:0) | ||
| 2nd (2nd leg) | Drogheda United | - | Cabinteely FC | 5:1 (1:0) | ||
| 1st(1st leg): 18/10/2019 19:45 | 2nd (2nd leg): 25/10/2019 19:45 | Winner: Drogheda United | ||||
