| 1. Round | 15/09/2018 | Udinese Calcio [Youth] | - | Empoli FC [Youth] | 3:2 | ||||
| 2. Round | 22/09/2018 | Empoli FC [Youth] | - | SSC Napoli [Youth] | 0:2 | ||||
| 3. Round | 29/09/2018 | Empoli FC [Youth] | - | Genoa CFC [Youth] | 1:2 | ||||
| 5. Round | 20/10/2018 | Empoli FC [Youth] | - | Sassuolo Calcio [Youth] | 3:3 | ||||
| 6. Round | 26/10/2018 | Torino FC [Youth] | - | Empoli FC [Youth] | 3:0 | ||||
| 10. Round | 01/12/2018 | Empoli FC [Youth] | - | Juventus [Youth] | 4:4 | ||||
| 11. Round | 08/12/2018 | AS Roma [Youth] | - | Empoli FC [Youth] | 1:4 | ||||
| 12. Round | 14/12/2018 | Empoli FC [Youth] | - | AC Milan [Youth] | 1:1 | ||||
| 13. Round | 23/12/2018 | Chievo Verona [Youth] | - | Empoli FC [Youth] | 0:0 | ||||
| 14. Round | 12/01/2019 | Empoli FC [Youth] | - | US Palermo [Youth] | 3:2 | ||||
| 15. Round | 18/01/2019 | Atalanta [Youth] | - | Empoli FC [Youth] | 1:0 | ||||
| 23. Round | 30/03/2019 | Empoli FC [Youth] | - | Inter [Youth] | 1:1 | ||||
| 28. Round | 11/05/2019 | Empoli FC [Youth] | - | Chievo Verona [Youth] | 1:2 | ||||
| 30. Round | 25/05/2019 | Empoli FC [Youth] | - | Atalanta [Youth] | 2:4 |
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