By Bhekizenzo Zonele
Defending Carling Knockout champions Orlando Pirates will begin their title defence against Premiership newcomers Milford FC, while Mamelodi Sundowns face a rematch against the side that eliminated them from last season’s competition.
The round-of-16 draw, held at Langhams Lifestyle Estate in Fourways, Johannesburg, on Wednesday evening, confirmed eight fixtures involving all 16 Betway Premiership clubs.

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The opening round is scheduled for the weekend of 24 October, with the Premier Soccer League (PSL) expected to confirm individual match dates, venues and kick-off times.
Pirates enter the competition as defending champions after defeating Marumo Gallants 1-0 after extra time in last season’s final at Peter Mokaba Stadium.
Sundowns will host Gallants, who eliminated them at the same stage last season, winning 7-6 on penalties following a goalless draw.
The Carling Knockout has developed a reputation for producing unexpected results, with smaller clubs challenging established Premiership giants.
Stellenbosch FC won the competition in 2023, followed by Magesi FC in 2024 and Pirates in 2025.

This year’s tournament will also see newly promoted Milford FC and Kruger United make their Carling Knockout debuts.
AmaZulu coach Arthur Zwane warned against judging teams by their current league performances, emphasising the different challenges presented by knockout football.
“Cup games are very unpredictable,” Zwane said.
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His side will travel to face Kruger United, with AmaZulu looking to carry their strong league performances into the competition.
Stellenbosch coach Gavin Hunt echoed Zwane’s concerns ahead of his side’s encounter against Durban City, warning that underestimating opponents could prove costly.
“There’s always been a real unpredictability with this cup, and I think if you don’t treat it with the respect it deserves, you will come second,” Hunt said.

Elsewhere, Kaizer Chiefs will host TS Galaxy, while Golden Arrows face Chippa United. Polokwane City will take on Siwelele FC, and Sekhukhune United will host Richards Bay.
Full Carling Knockout round-of-16 draw:
- Kruger United vs AmaZulu
- Mamelodi Sundowns vs Marumo Gallants
- Golden Arrows vs Chippa United
- Durban City vs Stellenbosch FC
- Orlando Pirates vs Milford FC
- Polokwane City vs Siwelele FC
- Sekhukhune United vs Richards Bay
- Kaizer Chiefs vs TS Galaxy
The competition follows a straight knockout format, with the final scheduled for 9 December.










