| 1. Round | 06/08/1999 | Sanfrecce Hiroshima | - | JEF United Ichihara | 2:1 | ||||
| 2. Round | 13/08/1999 | JEF United Ichihara | - | Verdy Kawasaki | 3:4 aet |  |
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| 3. Round | 17/08/1999 | Bellmare Hiratsuka | - | JEF United Ichihara | 1:2 | ||||
| 4. Round | 20/08/1999 | JEF United Ichihara | - | Kyoto Purple Sanga | 2:1 aet | ||||
| 5. Round | 27/08/1999 | Kashiwa Reysol | - | JEF United Ichihara | 2:0 | ||||
| 6. Round | 03/09/1999 | JEF United Ichihara | - | Yokohama F. Marinos | 2:3 aet | |
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| 7. Round | 10/09/1999 | Shimizu S-Pulse | - | JEF United Ichihara | 2:1 aet | ||||
| 8. Round | 14/09/1999 | JEF United Ichihara | - | Cerezo Osaka | 2:0 | ||||
| 9. Round | 17/09/1999 | Júbilo Iwata | - | JEF United Ichihara | 1:2 aet | ||||
| 10. Round | 22/09/1999 | JEF United Ichihara | - | Kashima Antlers | 0:2 | ||||
| 11. Round | 29/10/1999 | JEF United Ichihara | - | Nagoya Grampus Eight | 1:2 |  |
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| 12. Round | 16/11/1999 | Urawa Red Diamonds | - | JEF United Ichihara | 1:0 | ||||
| 13. Round | 19/11/1999 | JEF United Ichihara | - | Vissel Kobe | 0:1 | ||||
| 14. Round | 22/11/1999 | Avispa Fukuoka | - | JEF United Ichihara | 0:5 | ||||
| 15. Round | 26/11/1999 | Gamba Osaka | - | JEF United Ichihara | 0:1 |
Japan