| 1. Round | 06/08/1999 | Kashiwa Reysol | - | Kashima Antlers | 2:1 |  |
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| 2. Round | 13/08/1999 | Urawa Red Diamonds | - | Kashiwa Reysol | 2:3 aet | ||||
| 3. Round | 17/08/1999 | Kashiwa Reysol | - | Nagoya Grampus Eight | 1:2 | |
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| 4. Round | 20/08/1999 | Gamba Osaka | - | Kashiwa Reysol | 1:0 | ||||
| 5. Round | 27/08/1999 | Kashiwa Reysol | - | JEF United Ichihara | 2:0 | ||||
| 6. Round | 03/09/1999 | Vissel Kobe | - | Kashiwa Reysol | 0:2 | ||||
| 10. Round | 21/09/1999 | Kyoto Purple Sanga | - | Kashiwa Reysol | 1:2 aet | ||||
| 13. Round | 26/10/1999 | Júbilo Iwata | - | Kashiwa Reysol | 0:1 | ||||
| 11. Round | 29/10/1999 | Kashiwa Reysol | - | Yokohama F. Marinos | 1:1 aet | |
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| 14. Round | 22/11/1999 | Kashiwa Reysol | - | Cerezo Osaka | 0:3 |
Romania