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.

A total of 38 teams from 38 CAF associations qualified for the tournament after winning their respective premier domestic cups.

The away goals rule was used to determine the victors in the event of a match being tied over the two-legs.

Africa Sports won the two-legged final 2-1 on aggregate.