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| 07.08.1999 | Spartak Subotica | - | Vojvodina | 1:0 | ||
| Radnički Niš | - | Proleter Zrenjanin | 1:3 | |||
| Radnički Kragujevac | - | Hajduk Rodić | 2:0 | |||
| FK Rad Beograd | - | FK Mogren Budva | 3:1 | |||
| FK Budućnost Podgorica | - | FK Smederevo | 1:1 | |||
| FK Sutjeska | - | Hajduk Beograd | 4:3 | |||
| FK Zemun | - | Milicionar | 2:2 | |||
| OFK Beograd | - | FK Obilić | 4:2 | |||
| FK Zeleznik | - | Borac Čačak | 5:3 | |||
| Partizan | - | FK Čukarički | 2:1 |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Proleter Zrenjanin | 2 | 2 | 0 | 0 | 6:1 | 5 | 6 |
| 2 |
|
FK Zeleznik | 2 | 2 | 0 | 0 | 7:3 | 4 | 6 |
| 3 |
|
FK Sutjeska | 2 | 1 | 1 | 0 | 6:5 | 1 | 4 |
| 4 |
|
FK Zemun | 2 | 1 | 1 | 0 | 4:3 | 1 | 4 |
| 5 |
|
Hajduk Beograd | 2 | 1 | 0 | 1 | 7:5 | 2 | 3 |
| 6 |
|
FK Rad Beograd | 2 | 1 | 0 | 1 | 3:2 | 1 | 3 |
| 7 |
|
Partizan | 1 | 1 | 0 | 0 | 2:1 | 1 | 3 |
|
Vojvodina | 2 | 1 | 0 | 1 | 2:1 | 1 | 3 | |
| 9 |
|
OFK Beograd | 2 | 1 | 0 | 1 | 4:4 | 0 | 3 |
| 10 |
|
Hajduk Rodić | 2 | 1 | 0 | 1 | 2:2 | 0 | 3 |
|
Radnički Kragujevac | 2 | 1 | 0 | 1 | 2:2 | 0 | 3 | |
| 12 |
|
FK Obilić | 2 | 1 | 0 | 1 | 3:4 | -1 | 3 |
| 13 |
|
Spartak Subotica | 2 | 1 | 0 | 1 | 1:3 | -2 | 3 |
| 14 |
|
FK Budućnost Podgorica | 2 | 0 | 2 | 0 | 2:2 | 0 | 2 |
| 15 |
|
Crvena Zvezda | 1 | 0 | 1 | 0 | 2:2 | 0 | 1 |
| 16 |
|
FK Čukarički | 2 | 0 | 1 | 1 | 3:4 | -1 | 1 |
| 17 |
|
FK Smederevo | 2 | 0 | 1 | 1 | 2:3 | -1 | 1 |
| 18 |
|
Borac Čačak | 2 | 0 | 1 | 1 | 5:7 | -2 | 1 |
| 19 |
|
FK Mogren Budva | 2 | 0 | 1 | 1 | 2:4 | -2 | 1 |
|
Milicionar | 2 | 0 | 1 | 1 | 2:4 | -2 | 1 | |
| 21 |
|
Radnički Niš | 2 | 0 | 0 | 2 | 2:7 | -5 | 0 |
