The third edition of the COSAFA-Cup , officially COSAFA Castle Cup 1999 , took place from July 4th to October 2nd, 1999 . Eight teams from South Africa played for the title of South African champion. Angola won its first title. The preliminary round took place from February 7th to May 28th.
For the final round of the tournament, the top two from the last tournament were automatically qualified. The remaining eight participants played in the first round, the four winners of which qualified for the finals. The remaining four played in a play-off round for the last two tournament places. The tournament was continued in a knockout system.
1st round / qualification
The first round took place from February 7th to May 28th, 1999. Lesotho, Angola, Swaziland and South Africa qualified for the finals in the first round.