| 1. Round | 21/09/1958 | Torino FC | - | US Alessandria 1912 | 6:1 | ||||
| 2. Round | 28/09/1958 | US Alessandria 1912 | - | ACF Fiorentina | 1:4 | ||||
| 3. Round | 05/10/1958 | SPAL Ferrara | - | US Alessandria 1912 | 1:1 | ||||
| 4. Round | 12/10/1958 | US Alessandria 1912 | - | Calcio Padova | 1:3 | ||||
| 5. Round | 19/10/1958 | AC Milan | - | US Alessandria 1912 | 5:1 |  |
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| 7. Round | 02/11/1958 | Udinese Calcio | - | US Alessandria 1912 | 1:0 | ||||
| 13. Round | 28/12/1958 | US Alessandria 1912 | - | Juventus | 2:2 | ||||
| 14. Round | 04/01/1959 | AS Roma | - | US Alessandria 1912 | 0:2 | ||||
| 16. Round | 18/01/1959 | Inter | - | US Alessandria 1912 | 1:0 | ||||
| 23. Round | 15/03/1959 | Genoa CFC | - | US Alessandria 1912 | 1:1 | |
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| 24. Round | 22/03/1959 | US Alessandria 1912 | - | Udinese Calcio | 1:1 | ||||
| 26. Round | 05/04/1959 | US Alessandria 1912 | - | AC Lanerossi Vicenza | 1:0 | ||||
| 28. Round | 19/04/1959 | Lazio Roma | - | US Alessandria 1912 | 0:2 |
Italy