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| H | Progrès Niedercorn | - | Cardiff Metropolitan | 1:0 (0:0) | ||
| R | Cardiff Metropolitan | - | Progrès Niedercorn | 2:1 (1:0) | ||
| H: 27.06.2019 19:30 | R: 04.07.2019 19:30 | Sieger: Progrès Niedercorn | ||||
| H | Barry Town United | - | Cliftonville FC | 0:0 (0:0) | ||
| R | Cliftonville FC | - | Barry Town United | 4:0 (2:0) | ||
| H: 27.06.2019 19:30 | R: 04.07.2019 20:45 | Sieger: Cliftonville FC | ||||
| H | UE Sant Julià | - | Europa FC | 3:2 (1:1) | ||
| R | Europa FC | - | UE Sant Julià | 4:0 (1:0) | ||
| H: 27.06.2019 20:00 | R: 04.07.2019 20:30 | Sieger: Europa FC | ||||
| H | KÍ Klaksvík | - | SP Tre Fiori | 5:1 (2:0) | ||
| R | SP Tre Fiori | - | KÍ Klaksvík | 0:4 (0:3) | ||
| H: 27.06.2019 20:00 | R: 04.07.2019 20:45 | Sieger: KÍ Klaksvík | ||||
| H | SP La Fiorita | - | UE Engordany | 0:1 (0:1) | ||
| R | UE Engordany | - | SP La Fiorita | 2:1 (1:0) | ||
| H: 27.06.2019 20:45 | R: 04.07.2019 19:30 | Sieger: UE Engordany | ||||
| H | Ballymena United | - | NSÍ Runavík | 2:0 (0:0) | ||
| R | NSÍ Runavík | - | Ballymena United | 0:0 (0:0) | ||
| H: 27.06.2019 20:45 | R: 04.07.2019 20:00 | Sieger: Ballymena United | ||||
| H | KF Prishtina | - | St. Joseph's FC | 1:1 (1:1) | ||
| R | St. Joseph's FC | - | KF Prishtina | 2:0 (0:0) | ||
| H: 27.06.2019 20:45 | R: 02.07.2019 17:45 | Sieger: St. Joseph's FC | ||||
