| 19.09.1999 (15:00): Esbjerg- Viborg 1-2 (0-1)
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| | M�LSCORERE | 0-1 Heine Fernandez (43) ; 1-1 Morten Skytte (51) ; 1-2 Heine Fernandez (74)
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| ESBJERG | Benny Gall; Henrik Jensen, Henrik Ipsen, Lars Jakobsen, Martin Jensen  , Søren Pallesen (80. Lars Sørensen), Jess Thorup, Simon Karkov, Kim Jensen, Søren Borup (57. Hans Henrik Andreasen), Kenni Sommer (33. Morten Skytte) | |
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| Viborg | Arkadiusz Onyszko; Morten Hamm , Ralf Pedersen, Palle Sørensen, Thomas Tengstedt, Morten Poulsen (68. Alex Nørlund), Thomas Frandsen (86. Dennis Hansen), Jakob Glerup Nielsen, Anders Winther (57. Klaus Kærgård), Heine Fernandez, Hans Eklund
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| Tilskuere | 5.216 | |
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| Dommer | Jan Hald
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| 19.09.1999 (15:00): Lyngby - AGF 3-1 (0-0)
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| | M�LSCORERE | 1-0 Stefan Bidstrup (54) ; 2-0 Christian Magleby (74) ; 2-1 Jacek Kacprzak (79) ; 3-1 Søren Hermansen (88) | |
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| Lyngby | Per Fahlström; Ulrich Vinzents, Martin Birn, Morten Petersen, Lennart Lynge Larsen, Nichlas Hindsberg, Stefan Bidstrup (69. René Tengstedt), Mikkel Bo Jensen (75. Rasmus Marvits), Martin Johansen (75. Thomas Andie), Christian Magleby, Søren Hermansen | |
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| AGF | Lars Windfeld; John Jensen, Ken Martin, �li Johannesen, Dennis Siim (76. Olafur Kristjansson), Kenneth Christiansen, Michael Nonbo, Anders Bjerre, Jacek Kacprzak, Frank Krogsdal (46. Bo Nielsen ), Tomas Ingi Tomasson (65. Eric Lind) | |
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| Tilskuere | 1.973 | |
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| Dommer | Claus Bo Larsen
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| 19.09.1999 (15:00): Silkeborg - OB 0-1 (0-0)
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| | M�LSCORERE | 0-1 Søren Andersen (80) | |
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| Silkeborg | Peter Kjær; Morten Bruun, Bora Zivkovic, Peter Sørensen, Thomas Røll Larsen, Jesper Thygesen (46. Jacob Juhl), Peder Knudsen (82. Kern Lyhne), Thomas Poulsen, Nocko Jokovic (60. Lars Brøgger), Peter Lassen, Henrik 'Tømrer' Pedersen | |
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| OB | Lars Høgh; Steen Nedergaard, Michael Hemmingsen , Jann Jensen, Ulrik Laursen, Andrew Tembo (14. Gregor Andrijevski), Sune Heilbo (77. Torben Sangild), Ulrik Pedersen, Nicolai Wael, Mwape Miti , Søren Andersen | |
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| Tilskuere | 3.988 | |
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| Dommer | Anders Mosegaard
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| 19.09.1999 (15:00): Vejle - AaB 2-2 (1-0)
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| | M�LSCORERE | 1-0 Dan Sørensen (19) ; 1-1 Anders Andersson (62) ; 2-1 Jesper Mikkelsen (63) ; 2-2 Brian Priske (64) | |
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| Vejle | Boye Habekost; Jan S�nksen, Kent Scholz, Jens Madsen, Dan Sørensen (54. René S. Andersen), Jesper Mikkelsen, Calle Facius , Jesper Ljung (46. Allan Dyring), Peter Christiansen, Kaspar Dalgas , Ulrik Balling (71. Jerry Brown) | |
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| AaB | Jimmy Nielsen; Brian Priske, Jozo Matovac, Thomas Bælum, Jens Jessen, Lars Thomsen (59. Henrik Rasmussen), Ståle Solbakken , Allan Gaarde (65. Søren Frederiksen), Anders Andersson , Andres Oper, Frank Strandli | |
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| Tilskuere | 2.793 | |
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| Dommer | Steen Pedersen
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| 19.09.1999 (17:15): AB - Herfølge 2-2 (2-0)
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| | M�LSCORERE | 1-0 Chris Hermansen (5) ; 2-0 Peter Rasmussen (27) ; 2-1 Thomas Knudsen (76) ; 2-2 Kenneth Jensen (88) | |
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| AB | Jan Hoffmann; Allan Olesen, Peter Frank , Martin Albrechtsen  , Jan Michaelsen (62. Peter Knudsen), Jan Bjur, Brian Steen Nielsen, Peter Rasmussen (58. Nicolai Stokholm), Jesper Sørensen, Abdul Sule (46. Rasmus Daugaard), Chris Hermansen | |
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| Herfølge | Jakup Mikkelsen; Kenneth Kastrup (70. Dan Lübbers), Henrik Lykke , Steven Lustü, Michael Thomsen, Lars Jakobsen, Tommy Schram, Jesper Heyde , Jesper Falck , Bo Henriksen (74. Thomas Knudsen), Kenneth Jensen | |
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| Tilskuere | 4.053 | |
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| Dommer | Kim Milton Nielsen
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| 20.09.1999 (19:00): Brøndby - FC København 3-1 (1-0)
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| | M�LSCORERE | 1-0 Bent Christensen (9) ; 1-1 Clement Cliford (55) ; 2-1 Bent Christensen (71) ; 3-1 Peter Madsen (77) | |
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| Brøndby | Mogens Krogh; Søren Colding, Per Nielsen, Vragel Da Silva, Dan Anton Johansen, Ole Bjur, Kim Daugaard , Peter Madsen (90. Søren Krogh), Thomas Lindrup (82. Mikkel Jensen), Ruben Bagger, Bent Christensen | |
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| FC København | Karim Zaza; Kim Madsen, Michael 'Mio' Nielsen, Diego Tur (46. Thomas Rytter), Niclas Jensen , Donatas Vencevicius, Carsten Hemmingsen, Claus Nielsen (48. Todi Jønsson), Thomas Thorninger (77. Martin B. Larsen), David Nielsen, Clement Cliford
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| Tilskuere | 16.163 | |
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| Dommer | Knud Stadsgaard
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Forside