| 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 | ||||
| 16. Round | 25/01/2019 | Empoli FC [Youth] | - | Udinese Calcio [Youth] | 2:0 | ||||
| 17. Round | 03/02/2019 | SSC Napoli [Youth] | - | Empoli FC [Youth] | 0:1 | ||||
| 18. Round | 09/02/2019 | Genoa CFC [Youth] | - | Empoli FC [Youth] | 2:1 | ||||
| 20. Round | 23/02/2019 | Sassuolo Calcio [Youth] | - | Empoli FC [Youth] | 1:2 | ||||
| 21. Round | 02/03/2019 | Empoli FC [Youth] | - | Torino FC [Youth] | 2:1 | ||||
| 22. Round | 09/03/2019 | ACF Fiorentina [Youth] | - | Empoli FC [Youth] | 3:1 | ||||
| 23. Round | 30/03/2019 | Empoli FC [Youth] | - | Inter [Youth] | 1:1 | ||||
| 24. Round | 06/04/2019 | Empoli FC [Youth] | - | Sampdoria [Youth] | 0:2 |  |
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| 25. Round | 20/04/2019 | Juventus [Youth] | - | Empoli FC [Youth] | 0:5 | ||||
| 28. Round | 11/05/2019 | Empoli FC [Youth] | - | Chievo Verona [Youth] | 1:2 | |
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| 29. Round | 18/05/2019 | US Palermo [Youth] | - | Empoli FC [Youth] | 0:0 | ||||
| 30. Round | 25/05/2019 | Empoli FC [Youth] | - | Atalanta [Youth] | 2:4 | |
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