| 5. Round | 19/10/1958 | AC Milan | - | US Alessandria 1912 | 5:1 | ||||
| 6. Round | 26/10/1958 | US Alessandria 1912 | - | Genoa CFC | 0:0 | ||||
| 7. Round | 02/11/1958 | Udinese Calcio | - | US Alessandria 1912 | 1:0 | ||||
| 8. Round | 16/11/1958 | US Alessandria 1912 | - | AS Bari | 2:1 | ||||
| 9. Round | 23/11/1958 | AC Lanerossi Vicenza | - | US Alessandria 1912 | 1:0 | ||||
| 10. Round | 30/11/1958 | US Alessandria 1912 | - | US Triestina | 4:3 | ||||
| 30. Round | 17/05/1959 | Juventus | - | US Alessandria 1912 | 2:2 | ||||
| 31. Round | 24/05/1959 | US Alessandria 1912 | - | AS Roma | 1:1 | ||||
| 32. Round | 28/05/1959 | US Alessandria 1912 | - | Bologna FC | 1:0 | ||||
| 33. Round | 02/06/1959 | US Alessandria 1912 | - | Inter | 1:1 | ||||
| 34. Round | 07/06/1959 | Sampdoria | - | US Alessandria 1912 | 3:1 |
Italy