Along the way there have been some shock defeats in the decider, not least to Baroka FC in 2018, Platinum Stars in 2013 and a young Ajax Cape Town in 2000.
Does this year feel different? Perhaps, they have enjoyed incredible success in the MTN8, winning the last four editions, and the Nedbank Cup in in recent times, but the return of the Carling Knockout to the football calendar in 2023 has only continued their difficulties in this competition.
They lost a penalty shoot-out to Richards Bay in the quarterfinals two years ago, and were shocked by eventual winners Magesi FC in the Last 16 in 2024.
This year they have seen off Siwelele (1-0) and Magesi (2-1) in two home fixtures that both proved more difficult than they might have been, and despite being favourites, Pirates coach Abdeslam Ouaddou is not looking beyond Saturday.
“Since we have not played the game, we cannot start thinking about the final yet," Ouaddou said. "It’s very important for us to prepare for the game, to analyse the opponents, and to respect all the teams.
“I think it’s going to be a very tough game. Because first of all we’re in Durban. They will be proud to play well against Orlando Pirates, they will also want to be one of the two teams in the final. For us, it’s important to be ambitious.
"Of course, we’ve won the first cup (this season, the MTN8), but all my players are ambitious and the club is ambitious to play this game and reach the final.”
Pirates’ single Carling Knockout victory came in 2011 when they beat BidVest Wits 3-1 in the final thanks to goals from Thulasizwe Mbuyane, Daine Klate and Isaac Chansa.
But for the rest there has been little cheer, despite their numerous final appearances.
They lost to Durban Bush Bucks in 1987, then to Mamelodi Sundowns in 1990. It took five years to return to the final and this time it was Wits who beat them 1-0.
They were then stunned by a young Ajax Cape Town 4-1 in a replay of the 2000 decider, and lost to Ajax again in 2008 and bitter rivals Kaizer Chiefs in 2010.
There was some respite with that 2011 success, but normal service resumed after that with shock final losses to Platinum Stars and Baroka.
There is no real explanation why their conversion rate is so poor. In the PSL era particularly they have got past the first round in 20 of the 26 competitions played since the 1996/97 season, taking into account the fact that there has been no trophy on offer between 2020 and 2022.
They have exited in the quarterfinals six times (23% of the time), and in the semifinals on eight occasions (31%). Their six final appearances (23%) in the PSL era have yielded just that one win.
They had a run of four first round exits in a row between 2001 and 2004 that will not have helped their cause – coming unstuck against Ajax, Umtata Bush Bucks, Manning Rangers and Mamelodi Sundowns respectively.
Their biggest wins in the PSL era have been 4-0 successes against Santos (1997), Jomo Cosmos (1998) and Lamontville Golden Arrows (2013).
Their heaviest defeats have been 3-1 against Chiefs (1998) and Sundowns twice (1999 & 2004).
In all, Pirates have played 81 games in the comeptition since 1996/97, winning 43, drawing 20 and losing 18. They have scored 130 goals and conceded 84.
