The Carling Knockout Cup takes centre stage on Tuesday, 27 October 2026, with Kaizer Chiefs, Orlando Pirates and Mamelodi Sundowns preparing for crucial last-16 encounters. All three clubs will enjoy home advantage as they battle to secure places in the quarter-finals.
The matches, scheduled to kick off at 19:00, promise an exciting evening of South African football. However, the three giants face opponents with their own ambitions, and previous meetings suggest that surprises cannot be ruled out.
Kaizer Chiefs Face TS Galaxy at FNB Stadium
Kaizer Chiefs will welcome TS Galaxy to FNB Stadium as they look to advance to the Carling Knockout Cup quarter-finals.
Amakhosi will draw confidence from their previous meeting with Galaxy in April 2026, when they secured a 2-0 Betway Premiership victory. Flávio da Silva and Glody Lilepo scored the goals that earned Chiefs the win.
Nevertheless, knockout football presents a different challenge. Chiefs will need to turn their home advantage into a strong performance if they are to avoid an early exit.
With expectations high among the Amakhosi faithful, progressing to the next round would provide a valuable boost. TS Galaxy, meanwhile, will be determined to spoil the hosts’ plans and claim a place in the last eight.
Mamelodi Sundowns Seek Revenge Against Marumo Gallants
Mamelodi Sundowns face one of the evening’s most intriguing challenges when they host Marumo Gallants at Loftus Versfeld.
The fixture brings back memories of last season’s Carling Knockout Cup, when Gallants eliminated Sundowns in the last 16. After the match ended 0-0, Gallants won the penalty shootout 7-6 to send the Tshwane giants crashing out of the competition.
Sundowns will be eager to avoid a repeat of that disappointment and make the most of playing at home. However, Gallants will take confidence from their previous success and will be hoping to deliver another upset.
The encounter gives Sundowns an opportunity to settle the score, while Gallants have a chance to prove that their previous victory was no fluke.
Orlando Pirates Begin Their Title Defence Against Milford FC
Defending champions Orlando Pirates will host Milford FC at the Orlando Amstel Arena, with a quarter-final place at stake.
The Buccaneers previously defeated Milford 2-0 on the opening day of the Betway Premiership season. Despite that result, Milford have shown encouraging form, having lost only two of their first nine league matches, according to the source report.
Pirates will be determined to keep their cup defence on track, but Milford have an opportunity to make a statement by eliminating one of South African football’s biggest clubs.
The visitors will need a disciplined performance to challenge the hosts, who will be looking to use their home advantage to move closer to retaining the trophy.
Carling Knockout Cup: Tuesday’s Fixtures and Kick-Off Times
All three matches are scheduled for Tuesday, 27 October 2026, with kick-off at 19:00.
- Kaizer Chiefs vs TS Galaxy — FNB Stadium
- Mamelodi Sundowns vs Marumo Gallants — Loftus Versfeld
- Orlando Pirates vs Milford FC — Orlando Amstel Arena
Four Teams Have Already Reached the Quarter-Finals
While the big three prepare for their matches, four clubs have already secured their places in the Carling Knockout Cup quarter-finals.
AmaZulu FC advanced after defeating Kruger United 1-0, while Sekhukhune United beat Richards Bay FC 3-1.
Golden Arrows also progressed in convincing fashion, thrashing Chippa United 4-0. Siwelele FC completed the group of early qualifiers after a goalless draw against Polokwane City, winning the penalty shootout 4-3.
Their progress means several quarter-final places remain available, setting up an important round of fixtures for the remaining contenders.
Durban City and Stellenbosch FC Complete the Round
The final last-16 fixture is scheduled for Wednesday, 28 October, when Durban City host Stellenbosch FC at Chatsworth Stadium. Kick-off is set for 19:00.
That match will complete the round and determine the final team to advance to the quarter-finals.
With Chiefs, Pirates and Sundowns all in action, Tuesday night could prove decisive in shaping the next stage of the competition. The pressure will be on the favourites to deliver, but their opponents will be determined to produce memorable cup upsets.
Which teams do you think will qualify for the Carling Knockout Cup quarter-finals? Will Chiefs, Pirates and Sundowns all progress, or are more surprises on the way?
