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Australia | Russian Cup 1999/00 |  |
1/64 finals
 | 07.06.1999 | Angusht (Nazran) | – | Avtodor (Vladikavkaz) | 0:1 (0:0) | ||
Prokhladny | |||||||
| 07.06.1999 | Don (Novomoskovsk) | – | Avangard (Kursk) | 3:0 (2:0) | ||
Novomoskovsk | |||||||
| 07.06.1999 | Druzhba (Maykop) | – | Kuban (Krasnodar) | 2:0 aet (0:0) | ||
Maykop | |||||||
| 07.06.1999 | FK Khimki (Khimki) | – | Dynamo (Saint Petersburg) | 2:0 (1:0) | ||
Khimki | |||||||
| 07.06.1999 | Metallurg-Metiznik (Magnitogorsk) | – | Neftekhimik (Nizhnekamsk) | 0:3 (0:2) | ||
Yekaterinburg | |||||||
| 07.06.1999 | Mosenergo (Moscow) | – | Kosmos (Elektrostal) | 2:2 aet (2:2, 2:2), pen. 4:3 | ||
Moscow | |||||||
| 07.06.1999 | Spartak-Chukotka (Moscow) | – | Spartak (Ryazan) | 1:0 aet (0:0) | ||
Zheleznodorozhny | |||||||
| 07.06.1999 | Zvezda (Irkutsk) | – | Metallurg (Novokuznetsk) | 1:0 (1:0) | ||
Irkutsk | |||||||
| 06.06.1999 | Energetik (Uren) | – | Energiya (Ulyanovsk) | 3:0 (2:0) | ||
Uren | |||||||
| 06.06.1999 | Lada (Tolyatti) | – | Iskra (Engels) | 3:0 (0:0) | ||
 | Tolyatti | ||||||
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