Pirates have famously struggled in the League Cup and its various guises down the years, lifting the trophy only twice since it was first played in 1982 as they prepare to host Sekhukhune United in their 2026 quarter-final on Saturday.
The second of those triumphs came last season when they beat Marumo Gallants 1-0 after extra time in the final.
But despite their modest trophy haul, only one team has beaten them outright in the competition since 2017, when Magesi FC stunned the Buccaneers with a 3-2 victory at Orlando Stadium in 2024.
There was, of course, no competition played between 2020 and 2022, but Pirates' four other exits since 2017 have all come via penalty shoot-outs.
They lost to Polokwane City after a 2-2 draw in 2017 and to Baroka FC in the final the following year, when the game also finished 2-2.
Remarkably, they were eliminated by Kaizer Chiefs in 2019, again on penalties following a 2-2 draw, before suffering the same fate against Richards Bay after a goalless stalemate in 2023.
It means their record since 2017 reads played 16, won 11, drawn four and lost just once. They have scored 26 goals and conceded 12.
Pirates also lost on penalties to Chiefs in 2015, Bloemfontein Celtic in 2012, Chiefs again in 2010 and Benoni Premier United in 2007.
That means they have lost their last eight penalty shoot-outs in the competition, a remarkable run stretching back almost two decades.
The last time they prevailed in a shoot-out was against Celtic in the quarter-finals of the Coca-Cola Cup in November 2005, when they won 4-2 on penalties after a goalless draw.
They will hope to avoid a similar fate when they host Sekhukhune United in Saturday's quarter-final, as they continue their bid to retain the trophy.