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| H (Match allé) | Cabinteely FC | - | Drogheda United | 1:1 (1:0) | ||
| R (match retour) | Drogheda United | - | Cabinteely FC | 5:1 (1:0) | ||
| H (Match allé): 18.10.2019 20:45 | R (match retour): 25.10.2019 20:45 | vainqueur: Drogheda United | ||||
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| H (Match allé) | Cabinteely FC | - | Drogheda United | 1:1 (1:0) | ||
| R (match retour) | Drogheda United | - | Cabinteely FC | 5:1 (1:0) | ||
| H (Match allé): 18.10.2019 20:45 | R (match retour): 25.10.2019 20:45 | vainqueur: Drogheda United | ||||
