Pirates take on Zambian champions Zanaco in Lusaka on Saturday in the first leg of their second round tie in the 2013 version of Africa's top competition.
This after they easily dispatched Comoros outfit Djabal FC 9-0 on aggregate, their joint highest biggest victory over two legs.
The Buccaneers took on Mufulira Wanderers from Zambia in the second round of the 1996 competition, when they were defending champions. They managed a 1-1 draw away from home and then recorded a 1-0 success in Soweto.
Current coach Roger de Sa would take that against Zanaco. Their first meeting against a fellow Cosafa country was the year they won it, 1995, when they beat the brilliantly named Eleven Men in Flight from Swaziland 5-0 on aggregate.
Until recently, they had not lost a two-legged tie against another side from the region. But Malawian side Bakili Bullets won on away goals after a 2-2 aggregate score in 2004 – followed by two embarrassing first round exits in 2010 and 2011.
The first was against Botswana side Gaborone United when they again lost on away goals after drawing 2-2 in Port Elizabeth. And they were then humbled 3-1 in the Windy City by Angolan side Recreativo Libolo and could only manage a 1-1 draw away.
Perhaps their most surprising loss in a single fixture came with a 3-2 defeat at the hands of Saint Denis from Reunion in 1996. Luckily they had won the home leg 2-0.
They also suffered a pair of 2-1 defeats at the hands of Angolan side Primeiro Agosto in the group stages of the 1997 competition.
PIRATES' OVERALL RECORD VS SOUTHERN AFRICAN TEAMS
P30 W19 D6 L5 GF63 GA23