Perennial league winners Mamelodi Sundowns are three points clear at the top of the 2025/26 Betway Premiership standings but completed their campaign with a 3-2 loss away to TS Galaxy in midweek.
Second-placed Pirates have the superior goal-difference and would end the Brazilians' eight-year long dominance with a game to spare with all three points in front of their own fans at the Amstel Orlando Arena.
Durban City will have other ideas, however, as they look to secure their place in next season's MTN8, currently in seventh place, but with as many as four teams hot on their heels.
Golden Arrows (37), Siwelele (33), Stellenbosch (33) and Richards Bay (33) are all still mathematically in with a chance of a top eight finish.
But while Abdeslam Ouaddou's charges are unbeaten in their last 11 league matches, Pitso Dladla's side haven't won their last six games, drawing three and losing three.
Pirates won the first-round fixture 2-0 with goals from Evidence Makgopa and Patrick Maswanganyi, and last overcame Magesi 3-0 as City were held to a goalless draw with Stellenbosch.
In team news, Bucs will be without Tapelo Xoki and Sihle Nduli due to injury, while for City goalkeeper Darren Keet remains a doubt after his recent absence from the squad.
Ahead of the tie, a bullish Ouaddou said his team are determined to win the title for their fans.
“We still have two games and definitely we want to make our fans happy. You know, 15 years or 14 years without a league title – I think we can start to smell it, we are close but we cannot touch the trophy yet," he said on SuperSport.
"So we still have two games, we will see what happens. Credit has to be given to the fantastic fans that have really helped us and we are going to fight for them until the end.
"We are very proud of them. I think it's a process of the club. This project of Orlando Pirates is well-managed by fantastic people who know football."
Dladla reflected on their last game, adding: "They (Stellenbosch) were really organised defensively and hard to break down. They got really physical as well.
"I think we were a bit anxious and wasn't calm inside the box. We created a lot of chances inside their box but we never took those.
"Honestly, that is something we need to work on as a team. We going to have to go back to the drawing board and spend a lot of time there."
