1999 CAF Cup Winners Cup

1999 CAF Cup Winners Cup


First Round (Mar 14 and 28)
Orlando Pirates 6-0 Defense Force XI (BOT)
Defence Force 1-3 Orlando Pirates (AGG: 9-1)

Second Round (May2 and 16)
 Orlando Pirates 3-1 Maxaquene (MOZ)
Maxaquene 4-4 Orlando Pirates (AGG: 5-7)

Quarter-finals (Sep 4 and 19)
Al Masry (EGY) 1-0 Orlando Pirates
Orlando Pirates 0-3 Al Masry (AGG: 1-3)

Semi-finals (Oct 10 and 24)
First Leg: Orlando Pirates 3-1 Africa Sports
Second Leg: Africa Sports 3-1 Orlando Pirates (Agg: 4-4 – PEN: 3-0)