1999 African Cup Winners' Cup

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.

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.

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.

Matches

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
Anges de Fatima	9-2	Union Vesper	6-0	3-2
Mogas 90 FC	0-1	LPRC Oilers	0-0	0-1
Bata Bullets	4-3	Hintsa	4-2	0-1
FC Djivan	1-3	Defence Force XI	0-0	1-3
AS Marsouins	6-3	Arsenal	5-0	1-3
Fire Brigade SC	4-4(2-3 pen)	St Michel United	2-2	2-2

The first legs were played from 12–14 March, and the second legs were played from 26–28 March 1999.

Matches

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
WA Tlemcen	2-4	Al-Shat	1-2	1-2
AS Mineurs	1-1(4-3 pen)	LPRC Oilers	1-0	0-1
FAR Rabat	2-1	ASC Yeggo	2-0	0-1
Wikki Tourists	4-1	Renaissance FC	4-0	0-1
Africa Sports	3-1	Stade Malien	2-0	1-1
Simba FC	3-2	Tanzania Stars	2-1	1-1
Dynamo Douala	3-1	Anges de Fatima	3-0	0-1
Club Africain	4-0	ASFB	3-0	1-0
Power Dynamos	7-3	St Michel United	6-1	1-2
Coffee FC	w/o[1]	AS Inter Star	-	-
Mathare United'	4-3	Bata Bullets	2-0	2-3
Petro Atlético	3-4	AS Dragons	2-0	1-4
Maxaquene	3-3(6-5 pen)	AS Marsouins	2-1	1-2
Orlando Pirates	9-1	Defence Force XI	6-0	3-1
Al-Masry	1-1(4-3 pen)	Al-Merreikh	1-0	0-1
Asante Kotoko	3-2	Ndzimba	2-0	1-2

Notes:

^{^[1]} Coffee FC withdrew before their first leg tie against AS Inter Star, handing AS Inter Star a walkover into the second round.

The first legs were played between from 30 April-2 May, and the second legs were played from 14–16 May 1999.

Matches

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
AS Mineurs	6-0	Al-Shat	3-0	3-0
Wikki Tourists	0-3	FAR Rabat	0-1	0-2
Simba FC	0-3	Africa Sports	0-1	0-2
Club Africain	6-1	Dynamo Douala	4-0	2-1
AS Inter Star	w/o[1]	Power Dynamos	-	-
AS Dragons	4-2	Mathare United	3-1	1-1
Orlando Pirates	7-5	Maxaquene	3-1	4-4
Asante Kotoko	1-1(2-4 pen)	Al-Masry	1-0	0-1

Notes:

^{^[1]} AS Inter Star withdrew before their first leg tie against Power Dynamos, handing Power Dynamos a walkover into the second round.

The first legs were played on 4 & 5 September, and the second legs were played from 19–26 September 1999.

Matches

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
Power Dynamos	2-3	Club Africain	1-1	1-2
AS Dragons	1-3	Al-Masry	1-0	0-3
Orlando Pirates	4-1	AS Mineurs	1-0	3-1
FAR Rabat	1-2	Africa Sports	1-1	0-1

The first legs were played on 10 October, and the second legs were played on 23 & 24 October 1999.

Matches

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
Club Africain	4-0	Al-Masry	0-0	4-0
Africa Sports	4-4(3-0 pen)	Orlando Pirates	3-1	1-3

• Results available on CAF Official Website
• Results available on RSSSF