| 1. Round | 21/09/1958 | Torino FC | - | US Alessandria 1912 | 6:1 | ||||
| 3. Round | 05/10/1958 | SPAL Ferrara | - | US Alessandria 1912 | 1:1 |  |
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| 4. Round | 12/10/1958 | US Alessandria 1912 | - | Calcio Padova | 1:3 | ||||
| 5. Round | 19/10/1958 | AC Milan | - | US Alessandria 1912 | 5:1 | ||||
| 10. Round | 30/11/1958 | US Alessandria 1912 | - | US Triestina | 4:3 | ||||
| 12. Round | 21/12/1958 | SSC Napoli | - | US Alessandria 1912 | 0:0 | ||||
| 11. Round | 24/12/1958 | US Alessandria 1912 | - | Lazio Roma | 0:2 | ||||
| 17. Round | 25/01/1959 | US Alessandria 1912 | - | Sampdoria | 1:1 | |
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| 18. Round | 01/02/1959 | US Alessandria 1912 | - | Torino FC | 0:0 | ||||
| 20. Round | 15/02/1959 | US Alessandria 1912 | - | SPAL Ferrara | 2:0 | |
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| 21. Round | 22/02/1959 | Calcio Padova | - | US Alessandria 1912 | 0:0 | ||||
| 22. Round | 08/03/1959 | US Alessandria 1912 | - | AC Milan | 1:2 | ||||
| 23. Round | 15/03/1959 | Genoa CFC | - | US Alessandria 1912 | 1:1 | ||||
| 24. Round | 22/03/1959 | US Alessandria 1912 | - | Udinese Calcio | 1:1 | ||||
| 25. Round | 29/03/1959 | AS Bari | - | US Alessandria 1912 | 1:0 | ||||
| 26. Round | 05/04/1959 | US Alessandria 1912 | - | AC Lanerossi Vicenza | 1:0 | ||||
| 27. Round | 12/04/1959 | US Triestina | - | US Alessandria 1912 | 2:0 |
Italy