1999 African Cup Winners' Cup
| Tournament details | |
|---|---|
| Dates | 31 January - 4 December 1999 |
| Teams | 38 (from 1 confederation) |
| Final positions | |
| Champions |
 Africa Sports (2nd title)
|
| Runners-up |
 Club Africain |
| Tournament statistics | |
| Matches played | 70 |
| Goals scored | 191 (2.73 per match) |
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. Of the 38 teams that qualified for the tournament 2 did not participate in it;
The tournament consisted of five rounds preceding a two-legged final.
The away goals rule was used to determine the victors in the event of a match being tied over the two-legs. If it was not possible to determine a winner using the away goals rule, the tie went to a penalty shootout to determine the winner.
The first legs were played on 30 & 31 January, and the second legs were played on 14 February 1999.
The first legs were played from 12-14 March, and the second legs were played from 26-28 March 1999.
Notes:
The first legs were played between from 30 April-2 May, and the second legs were played from 14-16 May 1999.
Notes:
The first legs were played on 4 & 5 September, and the second legs were played from 19-26 September 1999.
The first legs were played on 10 October, and the second legs were played on 23 & 24 October 1999.
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