| Group G | 20/08/1988 | Spezia Calcio 1906 | - | SSC Napoli | 1:3 | ||||
| Group G | 23/08/1988 | AS Bari | - | SSC Napoli | 2:0 | ||||
| Group G | 27/08/1988 | Sambenedettese | - | SSC Napoli | 0:2 | ||||
| Group G | 29/08/1988 | SSC Napoli | - | SS Barletta Calcio | 3:0 | ||||
| Group G | 02/09/1988 | SSC Napoli | - | Bologna FC | 1:0 | ||||
| Group 2 | 13/09/1988 | US Lecce | - | SSC Napoli | 1:1 |  |
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| Group 2 | 20/09/1988 | SSC Napoli | - | AC Cesena | 2:0 | ||||
| Group 2 | 28/09/1988 | Modena FC | - | SSC Napoli | 0:4 | ||||
| Quarter-finals | 03/01/1989 | SSC Napoli | - | Ascoli Calcio | 3:0 |  |
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| Quarter-finals | 24/01/1989 | Ascoli Calcio | - | SSC Napoli | 3:1 | ||||
| Semi-finals | 31/01/1989 | Pisa SC | - | SSC Napoli | 0:2 | ||||
| Semi-finals | 07/02/1989 | SSC Napoli | - | Pisa SC | 1:0 | ||||
| Final | 06/06/1989 | SSC Napoli | - | Sampdoria | 1:0 | ||||
| Final | 27/06/1989 | Sampdoria | - | SSC Napoli | 4:0 |
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