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| 1st(1st leg) | Juventus | - | AC Venezia | 1:1 (1:0) | ||
| 2nd (2nd leg) | AC Venezia | - | Juventus | 2:2 (0:0, 1:1) aet | ||
| 1st(1st leg): 27/10/1998 | 2nd (2nd leg): 11/11/1998 | Winner: Juventus | ||||
| 1st(1st leg) | Sampdoria | - | Bologna FC | 0:0 (0:0) | ||
| 2nd (2nd leg) | Bologna FC | - | Sampdoria | 2:1 (0:1) | ||
| 1st(1st leg): 28/10/1998 | 2nd (2nd leg): 11/11/1998 | Winner: Bologna FC | ||||
| 1st(1st leg) | ACF Fiorentina | - | US Lecce | 1:0 (0:0) | ||
| 2nd (2nd leg) | US Lecce | - | ACF Fiorentina | 0:4 (0:0) | ||
| 1st(1st leg): 28/10/1998 | 2nd (2nd leg): 10/11/1998 | Winner: ACF Fiorentina | ||||
| 1st(1st leg) | Atalanta | - | AS Roma | 1:1 (1:1) | ||
| 2nd (2nd leg) | AS Roma | - | Atalanta | 4:5 (0:0, 1:1, 1:1) pso | ||
| 1st(1st leg): 28/10/1998 | 2nd (2nd leg): 12/11/1998 | Winner: Atalanta | ||||
| 1st(1st leg) | Udinese Calcio | - | Vicenza Calcio | 0:0 (0:0) | ||
| 2nd (2nd leg) | Vicenza Calcio | - | Udinese Calcio | 0:1 (0:0) | ||
| 1st(1st leg): 28/10/1998 | 2nd (2nd leg): 11/11/1998 | Winner: Udinese Calcio | ||||
| 1st(1st leg) | AS Bari | - | Parma AC | 1:2 (0:0) | ||
| 2nd (2nd leg) | Parma AC | - | AS Bari | 0:0 (0:0) | ||
| 1st(1st leg): 28/10/1998 | 2nd (2nd leg): 11/11/1998 | Winner: Parma AC | ||||
| 1st(1st leg) | Inter | - | Castel di Sangro | 1:0 (1:0) | ||
| 2nd (2nd leg) | Castel di Sangro | - | Inter | 1:1 (0:0) | ||
| 1st(1st leg): 28/10/1998 | 2nd (2nd leg): 11/11/1998 | Winner: Inter | ||||
| 1st(1st leg) | Lazio Roma | - | AC Milan | 3:1 (1:1) | ||
| 2nd (2nd leg) | AC Milan | - | Lazio Roma | 1:1 (0:1) | ||
| 1st(1st leg): 29/10/1998 | 2nd (2nd leg): 11/11/1998 | Winner: Lazio Roma | ||||
