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| 1st(1st leg) | Lucchese | - | SSC Napoli | 2:2 | ||
| 2nd (2nd leg) | SSC Napoli | - | Lucchese | 0:2 | ||
| 1st(1st leg): 22/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Lucchese | ||||
| 1st(1st leg) | Ancona Calcio | - | Ravenna Calcio | 0:1 | ||
| 2nd (2nd leg) | Ravenna Calcio | - | Ancona Calcio | 4:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Ravenna Calcio | ||||
| 1st(1st leg) | AC Lumezzane | - | Cagliari Calcio | 3:1 | ||
| 2nd (2nd leg) | Cagliari Calcio | - | AC Lumezzane | 2:0 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Cagliari Calcio | ||||
| 1st(1st leg) | AS Livorno | - | Reggina Calcio | 1:1 | ||
| 2nd (2nd leg) | Reggina Calcio | - | AS Livorno | 3:0 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Reggina Calcio | ||||
| 1st(1st leg) | ASG Nocerina | - | Hellas Verona | 2:2 | ||
| 2nd (2nd leg) | Hellas Verona | - | ASG Nocerina | 2:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Hellas Verona | ||||
| 1st(1st leg) | Calcio Padova | - | AC Reggiana | 2:1 | ||
| 2nd (2nd leg) | AC Reggiana | - | Calcio Padova | 5:6 (1:1, 2:1, 2:1) pso | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Calcio Padova | ||||
| 1st(1st leg) | US Cremonese | - | Atalanta | 0:2 | ||
| 2nd (2nd leg) | Atalanta | - | US Cremonese | 2:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Atalanta | ||||
| 1st(1st leg) | Chievo Verona | - | US Foggia | 0:0 | ||
| 2nd (2nd leg) | US Foggia | - | Chievo Verona | 1:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Chievo Verona | ||||
| 1st(1st leg) | SS Gualdo | - | AS Fidelis Andria | 1:1 | ||
| 2nd (2nd leg) | AS Fidelis Andria | - | SS Gualdo | 0:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: SS Gualdo | ||||
| 1st(1st leg) | Atletico Catania | - | Brescia Calcio | 0:1 | ||
| 2nd (2nd leg) | Brescia Calcio | - | Atletico Catania | 4:0 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Brescia Calcio | ||||
| 1st(1st leg) | Alzano Virescit | - | Torino FC | 1:1 | ||
| 2nd (2nd leg) | Torino FC | - | Alzano Virescit | 2:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Torino FC | ||||
| 1st(1st leg) | Cosenza Calcio | - | Treviso FBC | 1:1 | ||
| 2nd (2nd leg) | Treviso FBC | - | Cosenza Calcio | 2:2 aet | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Cosenza Calcio | ||||
| 1st(1st leg) | Castel di Sangro | - | AC Perugia | 1:0 | ||
| 2nd (2nd leg) | AC Perugia | - | Castel di Sangro | 1:1 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Castel di Sangro | ||||
| 1st(1st leg) | AC Cesena | - | Pescara Calcio | 2:2 | ||
| 2nd (2nd leg) | Pescara Calcio | - | AC Cesena | 0:3 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: AC Cesena | ||||
| 1st(1st leg) | AC Monza | - | US Lecce | 0:2 | ||
| 2nd (2nd leg) | US Lecce | - | AC Monza | 0:0 | ||
| 1st(1st leg): 23/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: US Lecce | ||||
| 1st(1st leg) | Ternana Calcio | - | Genoa CFC | 1:1 | ||
| 2nd (2nd leg) | Genoa CFC | - | Ternana Calcio | 3:2 | ||
| 1st(1st leg): 24/08/1998 | 2nd (2nd leg): 30/08/1998 | Winner: Genoa CFC | ||||
