The Buccaneers will also face Renaissance Berkane, the side that beat them in the CAF Confederation Cup final in 2021/22, as well as Cameroonian outfit Colombe Sportive.
Pirates beat Simba on penalties in the quarter-finals of the Confederation Cup four years ago before losing to Berkane via spot-kicks in the decider that same year.
Colombe Sportive will be facing South African opposition for the first time.
South African coach Barker left Stellenbosch to take charge of Simba in December 2025, having guided the Winelands club to the semi-finals of the Confederation Cup in 2024/25, where they lost to the Tanzanian side.
Here is the record of Berkane and Simba against South African clubs.
RS Berkane
The Moroccans are unbeaten against South African opposition, with three wins and two draws in their five previous clashes. They have scored 11 goals in that time and conceded only two.
That includes the one-off Confederation Cup final against Pirates in 2021/22 and fixtures against Sekhukhune United and Stellenbosch FC.
They clashed with Sekhukhune in the group stage of the Confederation Cup in 2023/24 and won 2-0 at home before a 0-0 draw away.
The following year, they faced Stellenbosch and comfortably beat them 3-1 away and 5-0 at home.
The fact they have scored more than two goals per game on average and kept clean sheets in three of the five matches is ominous.
Simba SC
Simba have a longer history with South African sides, having played Santos, Kaizer Chiefs, Pirates and Stellenbosch in the past.
They are unbeaten at home, having won three and drawn the other of their four matches. They did not concede a goal in any of those games.
That being said, they are winless in South Africa and have never scored a goal in the country either.
They had an epic tie with Santos in the Champions League in 2003 when they drew both legs 0-0 and then won 9-8 on penalties.
Against Chiefs in 2020/21, they lost 4-0 in South Africa but won 3-0 at home and were eliminated 4-3 on aggregate.
They lost their quarter-final against Pirates in 2021/22 on penalties after the sides traded 1-0 home victories.
Simba then faced Barker’s Stellenbosch in the semi-finals in 2024/25 and won 1-0 at home before holding their opponents to a 0-0 draw away.