| Group F | 23/08/1988 | C.G. Virescit Boccaleone | - | Pisa SC | 1:1 | ||||
| Group F | 27/08/1988 | Pisa SC | - | ACF Fiorentina | 4:2 |  |
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| Group F | 30/08/1988 | Genoa CFC | - | Pisa SC | 1:1 | ||||
| Group F | 02/09/1988 | Pisa SC | - | US Avellino | 1:1 | ||||
| Group 3 | 13/09/1988 | Pisa SC | - | AS Roma | 3:1 | |
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| Group 3 | 20/09/1988 | Pescara Calcio | - | Pisa SC | 2:2 | ||||
| Group 3 | 28/09/1988 | Pisa SC | - | Ancona Calcio | 1:1 | ||||
| Quarter-finals | 03/01/1989 | Hellas Verona | - | Pisa SC | 2:1 | ||||
| Quarter-finals | 24/01/1989 | Pisa SC | - | Hellas Verona | 1:0 | ||||
| Semi-finals | 31/01/1989 | Pisa SC | - | SSC Napoli | 0:2 |
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