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| H | Udinese Calcio | - | Parma AC | 3:2 (1:1) | ||
| R | Parma AC | - | Udinese Calcio | 4:0 (2:0) | ||
| H: 01.12.1998 | R: 27.01.1999 | Sieger: Parma AC | ||||
| H | Atalanta | - | ACF Fiorentina | 3:2 (1:2) | ||
| R | ACF Fiorentina | - | Atalanta | 1:0 (1:0) | ||
| H: 02.12.1998 | R: 28.01.1999 | Sieger: ACF Fiorentina | ||||
| H | Lazio Roma | - | Inter | 2:1 (1:1) | ||
| R | Inter | - | Lazio Roma | 5:2 (2:2) | ||
| H: 03.12.1998 | R: 27.01.1999 | Sieger: Inter | ||||
| H | Juventus | - | Bologna FC | 1:2 (1:0) | ||
| R | Bologna FC | - | Juventus | 0:1 (0:0) | ||
| H: 13.01.1999 | R: 26.01.1999 | Sieger: Bologna FC | ||||
