COSAFA Castle Cup 1999
Angola, Botswana, Lesotho, Malawi, Mozambique, Namibia, South Africa, Swaziland, Zambia (Holder) & Zimbabwe (10)
| Saturday, 7 February 1999 | ||||
| Lesotho | 1-0 | Namibia | ||
| 1-0 | ||||
| Maseru (Lesotho) | ||||
| Lesotho (Host) (Quarter-Finals) Namibia (2nd Round) | ||||
| Saturday, 20 February 1999 | ||||
| Botswana | 1-2 | South Africa | ||
| 1-2 | ||||
| Gaborone (Botswana) | ||||
| South Africa (Quarter-Finals) Botswana (Host) (2nd Round) | ||||
| Sunday, 25 April 1999 | ||||
| Malawi | 1-2 | Angola | ||
| 0-0 | ||||
| Blantyre (Malawi) | ||||
| Angola (Quarter-Finals) Malawi (Host) (2nd Round) | ||||
| Saturday, 8 May 1999 | ||||
| Swaziland | 3-1 | Mozambique | ||
| 2-0 | ||||
| Mbabane (Swaziland) | ||||
| Swaziland (Host) (Quarter-Finals) Mozambique (2nd Round) | ||||
| Sunday, 23 May 1999 | ||||
| Malawi | 1-1 | Namibia | ||
| 1-1 | ||||
| Namiba 4-2 on Penalty Shoot Out | ||||
| Blantyre (Malawi) | ||||
| Namibia (Quarter-Finals) | ||||
| Saturday, 29 May 1999 | ||||
| Botswana | 0-2 | Mozambique | ||
| 0-2 | ||||
| Gaborone (Botswana) | ||||
| Mozambique (Quarter-Finals) | ||||
| Sunday, 4 July 1999 | ||||
| Lesotho | 0-1 | Angola | ||
| 0-1 | ||||
| Maseru (Lesotho) | ||||
| Angola (Semi-Finals) | ||||
| Sunday, 18 July 1999 | ||||
| Swaziland | 1-1 | Zimbabwe | ||
| 0-0 | ||||
| Swaziland 4-3 on Penalty Shoot Out | ||||
| Mbabane (Swaziland) | ||||
| Swaziland (Host) (Semi-Finals) | ||||
| Saturday, 31 July 1999 | ||||
| Namibia | 1-1 | South Africa | ||
| 0-0 | ||||
| Namibia 4-1 on Penalty Shoot Out | ||||
| Windhoek (Namibia) | ||||
| Namibia (Host) (Semi-Finals) | ||||
| Saturday, 7 August 1999 | ||||
| Zambia | 1-1 | Mozambique | ||
| 0-1 | ||||
| Zambia 4-3 on Penalty Shoot Out | ||||
| Lusaka (Zambia) | ||||
| Zambia (Host & Holder) (Semi-Finals) | ||||
| Saturday, 14 August 1999 | ||||
| Zambia | 0-1 | Angola | ||
| 0-1 | ||||
| Lusaka (Zambia) | ||||
| Angola (Final) | ||||
| Saturday, 28 August 1999 | ||||
| Namibia | 1-1 | Swaziland | ||
| 0-0 | ||||
| Swaziland 4-2 on Penalty Shoot Out | ||||
| Windhoek (Namibia) | ||||
| Namibia (Host) (Final) | ||||
| Sunday, 26 September 1999 | ||||
| Angola | 1-0 | Namibia | ||
| 1-0 | ||||
| Luanda (Angola) | ||||
| Saturday, 2 October 1999 | ||||
| Namibia | 1-1 | Angola | ||
| 1-0 | ||||
| 1-0 | ||||
| Aggregate: 1-2 | ||||
| Windhoek (Namibia) | ||||
| 1st Angola 2nd Namibia | ||||