 | COSAFA Senior Challenge Cup 1999 | |
Final
 | 02.10.1999 |  | Namibia | – | Angola |  | 1:1 aet (1:0, 1:0) |
Windhoek | |||||||
| 26.09.1999 | | Angola | – | Namibia | | 1:0 (1:0) |
Luanda | |||||||
Semifinal
| 28.08.1999 | | Namibia | – | Swaziland |  | 1:1 (0:0), pen. 4:2 |
Windhoek | |||||||
| 14.08.1999 |  | Zambia | – | Angola | | 0:1 (0:0) |
Lusaka | |||||||
Quarterfinal
| 07.08.1999 | | Zambia | – | Mozambique |  | 1:1 (0:1), pen. 4:3 |
Lusaka | |||||||
| 31.07.1999 | | Namibia | – | South Africa |  | 1:1 (0:1), pen. 4:1 |
Windhoek | |||||||
| 18.07.1999 | | Swaziland | – | Zimbabwe |  | 1:1 (0:0), pen. 4:3 |
Lobamba | |||||||
| 04.07.1999 |  | Lesotho | – | Angola | | 0:1 (0:1) |
Maseru | |||||||
Second round
| 30.05.1999 |  | Botswana | – | Mozambique | | 0:2 (0:2) |
Gaborone | |||||||
| 22.05.1999 |  | Malawi | – | Namibia | | 1:1 (1:1), pen. 2:4 |
Blantyre | |||||||
First Round
| 09.05.1999 | | Swaziland | – | Mozambique | | 3:1 (2:0) |
Lobamba | |||||||
| 24.04.1999 | | Malawi | – | Angola | | 1:2 (1:0) |
Blantyre | |||||||
| 20.02.1999 | | Botswana | – | South Africa | | 1:2 (1:2) |
Gaborone | |||||||
| 07.02.1999 | | Lesotho | – | Namibia | | 1:0 (1:0) |
Maseru | |||||||
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