South African football fans are in for a blockbuster night of cup action when Mamelodi Sundowns, Orlando Pirates and Kaizer Chiefs all take to the field on Tuesday, 27 October, in the Carling Knockout Cup Round of 16.
The three Betway Premiership giants will be in action simultaneously, with all three matches scheduled to kick off at 19:00.
Mamelodi Sundowns will host Marumo Gallants at Loftus Versfeld, Orlando Pirates will welcome Milford FC to Orlando Amstel Arena, while Kaizer Chiefs face TS Galaxy at FNB Stadium.
With a place in the quarter-finals at stake, the evening promises plenty of intrigue as the three clubs look to keep their cup ambitions alive.
Mamelodi Sundowns face Marumo Gallants test
Mamelodi Sundowns will have home advantage when they take on Gallants in Pretoria.
The Brazilians will be eager to progress in a competition that offers another opportunity to add silverware to their collection.
However, Marumo Gallants, last season’s beaten finalists, will be determined to upset the odds and book their place in the next round.
Orlando Pirates begin title defence
Defending champions Orlando Pirates will also be in action on Tuesday night when they face Milford FC at Orlando Amstel Arena.
The Buccaneers won last season’s Carling Knockout Cup after beating Marumo Gallants 1-0 in the final. They will now be looking to take another step towards retaining the trophy.
Milford, meanwhile, will have the chance to make a statement against one of South Africa’s biggest clubs.
Kaizer Chiefs face TS Galaxy
Kaizer Chiefs complete the trio of headline fixtures when they host TS Galaxy at FNB Stadium.
The Soweto giants will be hoping to progress in the knockout competition, but TS Galaxy will provide a challenging test as both teams target a place in the quarter-finals.
Carling Knockout Round of 16 fixtures
The Round of 16 begins on Saturday, 24 October, with Golden Arrows taking on Chippa United at King Zwelithini Stadium at 15:00. Polokwane City will then face Siwelele FC at Old Peter Mokaba Stadium at 18:00.
Sunday’s fixtures see Kruger United meet AmaZulu FC at Mbombela Stadium at 15:00, followed by Sekhukhune United against Richards Bay FC at New Peter Mokaba Stadium at 18:00.
Durban City will host Stellenbosch FC at Chatsworth Stadium on Wednesday, 28 October, at 19:00.
All Round of 16 matches will be decided over 90 minutes. If a match is all-square at full-time, extra time will be played, followed by a penalty shootout if necessary.
With three of the country’s biggest clubs all in action on the same night, Tuesday promises to be one of the standout dates on the Carling Knockout Cup calendar.
Mark it down now!
The dates, kick-off times and venues for the #CarlingKnockoutCup Last 16 are locked in.
— Official PSL (@OfficialPSL) October 20, 2026
Ticket information will be confirmed in due course. pic.twitter.com/96MXhAAtTM