1999 African Cup Winners' Cup
The 1999 African Cup Winners' Cup was the twenty-fifth season of Africa's second oldest club football tournament organised by CAF.
Ivorian club Africa Sports appeared in and won their second African Cup Winners' Cup title after defeating former African champions Club Africain of Tunisia 2-1 over the two-legged final.
Association team allocation
A total of 38 teams from 38 CAF associations qualified for the tournament after winning their respective premier domestic cups. Of the 38 teams that qualified for the tournament 2 did not participate in it;- Ethiopian club Coffee FC, who were set to appear in the first round, withdrew before their first leg tie with AS Inter Star.
- Burundian club AS Inter Star, who had received a bye into the second round following the withdrawal of Coffee FC, would themselves withdraw before their first leg tie with Power Dynamos.
Format
The tournament consisted of five rounds preceding a two-legged final.- Preliminary round - The 12 lowest ranked teams - whose rankings were determined by their association's performances at previous CAF club tournaments - were drawn against each other in 6 matches consisting of two-legs each.
- First round - The 6 winners from the preliminary round were then drawn against the remaining 26 clubs, resulting in 16 matches consisting of two-legs each.
- Second round - The 16 winners from the first round were then drawn against each other, resulting in 8 matches consisting of two-legs each.
- Quarter-finals - The 8 winners from the second round were then drawn against each other, resulting in 4 matches consisting of two-legs each.
- Semi-finals - The 4 victorious quarter-finalists were then drawn against each other in 2 semi-finals consisting of two-legs each.
- Final - The victorious semi-finalists contested a two-legged final to determine the champion.