The 1998 African Cup Winners' Cup was the twenty-fourth season of Africa's second oldest club football tournament organised by CAF. As before, the tournament was open to clubs that won their nation's premier domestic cup. Espérance of Tunisia won the cup after defeating Angola's Primeiro de Agosto 4-2 in a two-legged final. It was Espérance's first Cup Winners' Cup triumph and their fourth African club title while Primeiro de Agosto made their first appearance in a continental final.
Association team allocation
A total of 39 teams from 39 CAF associations qualified for the tournament after winning their respective premier domestic cups. Of the 39 teams that qualified for the tournament 4 would not participate in it while 1 withdrew and was replaced by another club from its association;
Congolese club AS Vita Club, who were also due to appear in the Preliminary Round, withdrew before the tournament started.
The Senegalese Football Federation withdrew its representative before the tournament began. The name of the club that was to represent Senegal was never given
Gambian club Hawks, who were set to appear in the First Round, withdrew before their first leg tie with U.S.M. Alger.
Kaizer Chiefs were originally set to represent South Africa but they withdrew before the tournament started. Their place was taken by the team they defeated in the cup final that qualified them for the tournament, Mamelodi Sundowns.
Format
The tournament consisted of five rounds preceding a two-legged final.
Preliminary round - The 14 lowest ranked teams - whose rankings were determined by their association's performances at previous CAF club tournaments - were drawn against each other in 7 matches consisting of two-legs each.
First round - The 7 winners from the preliminary round were then drawn against the remaining 25 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.
Preliminary round
The first legs were played from 30 January-2 February, and the second legs were played from 13–15 February 1998.
Matches
First round
The first legs were played from 20–22 March, and the second legs were played from 3–5 April 1998.
Matches
Second round
The first legs were played from 24–26 April, and the second legs were played from 8–10 May 1998 with the exception of the second leg between Mbilinga FC and AS Dragons, which was played on May 12.
Matches
Quarter-finals
The first legs were played from 4–6 September, and the second legs were played from 18–20 September 1998.
Matches
Semi-finals
The first legs were played on 10 & 11 October, and the second legs were played between on 23 & 25 October 1998.
Matches
Final
First leg
Second leg
Esperance won the two-legged final 4-2 on aggregate.
