| Group H | 20/08/1988 | US Arezzo | - | Sampdoria | 0:2 |  |
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| Group H | 23/08/1988 | Sampdoria | - | US Cremonese | 5:0 | |
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| Group H | 27/08/1988 | US Lecce | - | Sampdoria | 0:0 | ||||
| Group H | 30/08/1988 | Sampdoria | - | Modena FC | 4:1 | |
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| Group H | 02/09/1988 | Calcio Padova | - | Sampdoria | 1:3 | ||||
| Group 4 | 13/09/1988 | Sampdoria | - | Atalanta | 1:0 |  |
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| Group 4 | 20/09/1988 | AS Bari | - | Sampdoria | 1:1 | ||||
| Group 4 | 28/09/1988 | Sampdoria | - | AC Monza | 3:0 | ||||
| Quarter-finals | 03/01/1989 | Sampdoria | - | ACF Fiorentina | 3:0 | ||||
| Quarter-finals | 24/01/1989 | ACF Fiorentina | - | Sampdoria | 1:1 | ||||
| Semi-finals | 31/01/1989 | Atalanta | - | Sampdoria | 2:3 | |
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| Semi-finals | 07/02/1989 | Sampdoria | - | Atalanta | 3:1 | ||||
| Final | 06/06/1989 | SSC Napoli | - | Sampdoria | 1:0 | ||||
| Final | 27/06/1989 | Sampdoria | - | SSC Napoli | 4:0 | |
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