| 1. Round | 21/09/1958 | Genoa CFC | - | SSC Napoli | 3:3 | ||||
| 2. Round | 28/09/1958 | SSC Napoli | - | AC Milan | 0:1 | ||||
| 3. Round | 05/10/1958 | SSC Napoli | - | Sampdoria | 3:2 | ||||
| 4. Round | 12/10/1958 | Juventus | - | SSC Napoli | 2:0 | ||||
| 5. Round | 19/10/1958 | SSC Napoli | - | AC Lanerossi Vicenza | 1:0 | ||||
| 6. Round | 26/10/1958 | Lazio Roma | - | SSC Napoli | 0:0 | ||||
| 10. Round | 30/11/1958 | SSC Napoli | - | SPAL Ferrara | 0:0 | ||||
| 11. Round | 07/12/1958 | US Triestina | - | SSC Napoli | 0:0 | ||||
| 12. Round | 21/12/1958 | SSC Napoli | - | US Alessandria 1912 | 0:0 | ||||
| 13. Round | 28/12/1958 | Bologna FC | - | SSC Napoli | 1:1 | ||||
| 14. Round | 04/01/1959 | Inter | - | SSC Napoli | 1:1 | ||||
| 15. Round | 11/01/1959 | SSC Napoli | - | Udinese Calcio | 1:1 | ||||
| 16. Round | 18/01/1959 | SSC Napoli | - | AS Bari | 1:2 | ||||
| 17. Round | 25/01/1959 | ACF Fiorentina | - | SSC Napoli | 4:1 |
Italy