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| U | Real Unión | - | Real Valladolid | 1:1 (1:1) | ||
| R | Real Valladolid | - | Real Unión | 0:1 (0:1) | ||
| U: 09.11.1999 20:30 | R: 01.12.1999 20:45 | Winnaars: Real Unión | ||||
| U | UD Alzira | - | Málaga CF | 0:0 (0:0) | ||
| R | Málaga CF | - | UD Alzira | 2:0 (0:0) | ||
| U: 09.11.1999 21:00 | R: 01.12.1999 21:00 | Winnaars: Málaga CF | ||||
| U | Club Bermeo | - | Real Betis | 0:0 (0:0) | ||
| R | Real Betis | - | Club Bermeo | 2:0 (2:0) | ||
| U: 10.11.1999 20:15 | R: 01.12.1999 21:00 | Winnaars: Real Betis | ||||
| U | Barakaldo CF | - | CE Premià | 1:0 (0:0) | ||
| R | CE Premià | - | Barakaldo CF | 2:2 (0:0) | ||
| U: 10.11.1999 20:15 | R: 01.12.1999 20:30 | Winnaars: Barakaldo CF | ||||
| U | CA Osasuna | - | Sevilla FC | 1:0 (1:0) | ||
| R | Sevilla FC | - | CA Osasuna | 1:1 (1:1) | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 21:00 | Winnaars: CA Osasuna | ||||
| U | CD Logroñés | - | Real Sociedad | 2:1 (0:1) | ||
| R | Real Sociedad | - | CD Logroñés | 0:1 (0:0) | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 20:15 | Winnaars: CD Logroñés | ||||
| U | SD Compostela | - | CD Numancia | 4:2 (1:1) | ||
| R | CD Numancia | - | SD Compostela | 3:2 (0:1) | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 20:30 | Winnaars: SD Compostela | ||||
| U | SD Ponferradina | - | Albacete | 1:1 (0:1) | ||
| R | Albacete | - | SD Ponferradina | 3:1 (0:1, 1:1) n.v. | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 21:00 | Winnaars: Albacete | ||||
| U | CD Ourense | - | Getafe CF | 1:0 (0:0) | ||
| R | Getafe CF | - | CD Ourense | 1:2 (1:1) | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 20:30 | Winnaars: CD Ourense | ||||
| U | Gimnástica Segoviana | - | Sporting Gijón | 0:0 (0:0) | ||
| R | Sporting Gijón | - | Gimnástica Segoviana | 2:1 (0:0) | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 20:30 | Winnaars: Sporting Gijón | ||||
| U | SD Eibar | - | CD Toledo | 1:0 (1:0) | ||
| R | CD Toledo | - | SD Eibar | 0:0 (0:0) | ||
| U: 10.11.1999 20:30 | R: 01.12.1999 21:00 | Winnaars: SD Eibar | ||||
| U | UD Salamanca | - | Rayo Vallecano | 2:2 (1:1) | ||
| R | Rayo Vallecano | - | UD Salamanca | 4:2 (1:0) | ||
| U: 10.11.1999 20:45 | R: 01.12.1999 21:00 | Winnaars: Rayo Vallecano | ||||
| U | Novelda CF | - | CP Almería | 0:1 (0:1) | ||
| R | CP Almería | - | Novelda CF | 0:0 (0:0) | ||
| U: 10.11.1999 20:45 | R: 01.12.1999 21:15 | Winnaars: CP Almería | ||||
| U | Talavera CF | - | CP Mérida | 1:0 (1:0) | ||
| R | CP Mérida | - | Talavera CF | 3:0 (0:0) | ||
| U: 10.11.1999 20:45 | R: 01.12.1999 21:00 | Winnaars: CP Mérida | ||||
| U | Recreativo Huelva | - | Real Zaragoza | 0:0 (0:0) | ||
| R | Real Zaragoza | - | Recreativo Huelva | 4:0 (1:0) | ||
| U: 10.11.1999 21:00 | R: 01.12.1999 20:30 | Winnaars: Real Zaragoza | ||||
| U | CF Extremadura | - | Deportivo Alavés | 1:1 (0:1) | ||
| R | Deportivo Alavés | - | CF Extremadura | 1:0 (0:0) | ||
| U: 10.11.1999 21:00 | R: 01.12.1999 20:30 | Winnaars: Deportivo Alavés | ||||
| U | UD Melilla | - | Athletic Club | 2:2 (1:1) | ||
| R | Athletic Club | - | UD Melilla | 3:2 (0:1) | ||
| U: 10.11.1999 21:00 | R: 01.12.1999 20:15 | Winnaars: Athletic Club | ||||
| U | Coria CF | - | UE Lleida | 2:4 (0:3) | ||
| R | UE Lleida | - | Coria CF | 1:1 (1:1) | ||
| U: 10.11.1999 21:00 | R: 01.12.1999 20:30 | Winnaars: UE Lleida | ||||
| U | Villarreal CF | - | CD Leganés | 0:1 (0:0) | ||
| R | CD Leganés | - | Villarreal CF | 0:3 (0:0, 0:1) n.v. | ||
| U: 10.11.1999 21:00 | R: 01.12.1999 21:00 | Winnaars: Villarreal CF | ||||
| U | Badajoz CF | - | UD Las Palmas | 1:1 (0:1) | ||
| R | UD Las Palmas | - | Badajoz CF | 1:0 (0:0) | ||
| U: 10.11.1999 21:00 | R: 30.11.1999 22:00 | Winnaars: UD Las Palmas | ||||
| U | Zamora CF | - | CD Tenerife | 2:2 (2:2) | ||
| R | CD Tenerife | - | Zamora CF | 4:0 (4:0) | ||
| U: 10.11.1999 21:00 | R: 01.12.1999 22:00 | Winnaars: CD Tenerife | ||||
| U | Córdoba CF | - | Espanyol | 1:1 (0:0) | ||
| R | Espanyol | - | Córdoba CF | 2:0 (2:0) | ||
| U: 10.11.1999 21:15 | R: 01.12.1999 20:30 | Winnaars: Espanyol | ||||
| U | Hércules CF | - | Racing Santander | 0:0 (0:0) | ||
| R | Racing Santander | - | Hércules CF | 3:0 (3:0) | ||
| U: 10.11.1999 21:15 | R: 01.12.1999 20:00 | Winnaars: Racing Santander | ||||
| U | Lorca CF | - | Real Oviedo | 0:1 (0:0) | ||
| R | Real Oviedo | - | Lorca CF | 2:0 (2:0) | ||
| U: 10.11.1999 21:30 | R: 01.12.1999 20:30 | Winnaars: Real Oviedo | ||||
