 | African Cup Winners' Cup 1999 | |
1/16 finals
 | 03.04.1999 |  | Al-Merreikh | – | Al-Masry |  | 1:0, pen. 3:4 |
| 28.03.1999 |  | Bata Bullets | – | Mathare United |  | 3:2 |
| 28.03.1999 |  | Dragons | – | Petro Atlético |  | 4:1 |
| 28.03.1999 |  | Ndzimba | – | Asante Kotoko |  | 2:1 |
| 28.03.1999 |  | Renaissance | – | Wikki Tourists |  | 1:0 |
| 27.03.1999 |  | ASF de Bobo | – | Club Africain |  | 0:1 |
| 27.03.1999 |  | Defence Force | – | Orlando Pirates |  | 1:3 |
| 27.03.1999 |  | Marsouins | – | Maxaquene |  | 2:1, pen. 5:6 |
| 27.03.1999 |  | Saint-Michel United | – | Power Dynamos |  | 2:1 |
| 27.03.1999 |  | Stade Malien | – | Africa Sports |  | 1:1 |
| 27.03.1999 |  | Tanzania Stars | – | Simba |  | 1:1 |
| 26.03.1999 |  | Al Shat | – | WA Tlemcen |  | 2:1 |
| 26.03.1999 |  | ASC Yeggo | – | FAR |  | 1:0 |
| 26.03.1999 |  | ASDR Fatima | – | Dynamo Douala |  | 1:0 |
|  | LPRC Oilers | – | AS Mineurs |  | 1:0, pen. 3:4 | |
Football calendar
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