Three clear days. Saturday, Sunday and Monday are all the big three get between a CAF Friday that broke two sets of hearts and a Tuesday night that asks them to go again. Chiefs supporters are still replaying a shoot-out in Durban. Sundowns fans are still staring at one away goal. Pirates fans are still smiling. And in KwaZulu-Natal, a club in its first Premiership season is packing for Soweto to face the champions. This knockout cup last 16 preview covers the four ties that finish the round, and not one of them is only about the cup.
Four quarter-final places are already gone. Golden Arrows and Siwelele went through on Saturday, as our Saturday recap tells it, and AmaZulu and Sekhukhune United joined them on Sunday. The other four are decided this week, with R6.85 million waiting for whoever lifts the trophy, according to Kaizer Chiefs and EWN.
| Quick facts | Date | Kick-off | Venue |
|---|---|---|---|
| Orlando Pirates v Milford | Tuesday 27 October | 19:00 SAST | Orlando Stadium, Soweto |
| Kaizer Chiefs v TS Galaxy | Tuesday 27 October | 19:00 SAST | FNB Stadium, Johannesburg |
| Mamelodi Sundowns v Marumo Gallants | Tuesday 27 October | 19:00 SAST | Loftus Versfeld, Pretoria |
| Durban City v Stellenbosch | Wednesday 28 October | 19:00 SAST | Chatsworth Stadium, Durban |
| Holders | Orlando Pirates |
Dates, times and venues are the PSL’s, and each home club lists the same details.
Knockout cup last 16 preview: why this round bites
Friday changed the week. Kaizer Chiefs beat Red Arrows 1-0 in Durban and still went out of the Confederation Cup, losing the shoot-out after a 1-1 aggregate, as our report from Moses Mabhida describes. Mamelodi Sundowns, champions of Africa in May, drew 1-1 with Wiliete at Loftus after a goalless first leg and fell on the away goal, the story told in our Wiliete report. Orlando Pirates thrashed African Stars 4-0 and are in the Champions League group stage. Durban City joined them in Africa’s group stages on Sunday, 6-1 on aggregate in the Confederation Cup.
And Saturday brings the Soweto Derby, Pirates against Chiefs at FNB Stadium at 15:30, the PSL confirms. Two Soweto clubs, two games in five days. Every selection on Tuesday will be made with one eye on the weekend.
Orlando Pirates v Milford: the champions meet the newcomers
Pirates are the league champions and the holders of this trophy, having beaten Marumo Gallants 2-0 in last year’s final in Mbombela, EWN recorded. They are second in the league, a point behind Sundowns with a game in hand, the PSL log shows, and have conceded one goal in eight league games, according to the club’s table.
They have beaten Milford once already, 2-0 at Orlando Stadium on the opening day, 1 August, the club’s results show. Since then the KwaZulu-Natal side have climbed to fourth, with 15 points from nine games, above Chiefs. Their most recent league game was a 1-0 win at Golden Arrows.
Abdeslam Ouaddou is not taking them lightly. “The advantage, the positive point is to play at home but I think it will be a difficult game,” he said, as quoted by the Sowetan on Monday. “They are a well-coached team, very disciplined and well-organised. They can run as well, so it will not be an easy game.”
Xanti Pupuma, Milford’s chairman and head coach, believes the side Pirates meet now is not the one they beat in August. “I’m not saying it would have made a difference, but now we’re going into this game full force,” he told the Daily Dispatch. “We have adjusted to the division, and I think we are in a better space than we were in the first game.”
Milford reached the Nedbank Cup semi-finals last season while still in the second tier, iDiski Times noted, and Pupuma is leaning on that: “Cup games are different from the league, you only have one chance, and they tend to be open.”
Team news: Pirates had published no squad or injury update by Monday morning. Before Friday’s game, Ouaddou said Oswin Appollis had trained without pain but would not be rushed. “They are all Ferraris, we need to take care of the engines very well,” he said, iDiski Times reported. The club has not said whether he plays on Tuesday. Follow the champions on our Orlando Pirates page.
Kaizer Chiefs v TS Galaxy: the club closes ranks
Chiefs needed a statement after Friday, and on Saturday the club issued one. Sporting Director Kaizer Motaung Jnr reaffirmed the club’s “full support for, and confidence in” head coach Fernando Da Cruz and his technical team. He wrote that on Friday, “despite the result and the injuries we carry, that warrior spirit was visible on the field,” and added a line aimed at the stands: “Now is the time for unity, not division.”
The league table tells a story of draws rather than defeats. Chiefs are unbeaten in eight league games, but five of them were draws, and they sit fifth.
On team news, the club said before Friday that goalkeeper Renaldo Leaner had been injured during preparations, while Brandon Petersen and Lebohang Maboe had recovered. It has not said whether Leaner is fit for Tuesday. Tickets are R60, the club says.
TS Galaxy arrive 13th, with one league win, and lost 3-0 at Pirates on 13 October. But Galaxy have a history with this opponent. Esau Mtsweni, who spoke for the club as caretaker coach after the draw, put it plainly to iDiski Times: “Anyone can win it and hopefully it will be us. And we’ve done it before; we can still do it again.”
He did not need to explain the reference. In May 2019 Galaxy, then a first-division side, beat Chiefs 1-0 in the Nedbank Cup final at Moses Mabhida Stadium with a Zakhele Lepasa penalty deep in stoppage time, TimesLIVE and SABC News reported. And Chiefs went out of this competition at the same stage last season, on penalties against Stellenbosch in Cape Town, SuperSport reported.
Mamelodi Sundowns v Marumo Gallants: a rematch with a sting
Sundowns are still top of the league and still MTN8 winners, having beaten Pirates 2-0 in the final on 10 October. But Friday hurt, and Miguel Cardoso did not hide it. “Great empires also come from ashes,” he said at his post-match press conference, as reported by TimesLIVE. “Maybe it’s an important lesson for looking ahead because, as I usually say, we are not what happens to us, we are much more what we do with what happens to us.”
Gallants know how to hurt Sundowns in this competition. The same tie was played in last year’s last 16, and Gallants won it 7-6 on penalties after 120 goalless minutes at Lucas Moripe Stadium, SuperSport and OFM reported. They went all the way to the final.
This time they arrive bottom of the league with two points and no win from eight games. Ronnie Kanalelo, the Namibian who left African Stars to replace Phuti Mohafe in September, insists the chances are coming. “I would be worried if we were not creating chances, but we are creating chances but let down by decision making in the final third,” he told the Sowetan.
Sundowns beat Gallants 2-0 at Loftus in the league in August, the club’s fixture list shows. Sundowns had published no squad or injury news for Tuesday by Monday morning. Next come Durban City on Saturday and USM Alger in the CAF Super Cup on 8 November. More on Masandawana on our Mamelodi Sundowns page.
Durban City v Stellenbosch: Hunt goes back to Durban
Durban City, the Nedbank Cup holders, come home from Mauritius with a first CAF group-stage place in the bag. Their head coach Eric Tinkler, announced by the club on 8 October, has said he will not rebuild the side. “I don’t want to make massive changes because the club was successful last season. It’s about giving others an opportunity and getting back to winning ways,” he told the Daily Sun when he arrived.
City sit 10th in the league. The visitors bring an old face. Gavin Hunt coached Durban City until early December last year, then replaced Steve Barker at Stellenbosch, BusinessDay reported. Stellenbosch won the first edition of this competition in 2023, and Hunt fancies another run. “It’s got quite a history of underdogs winning it, so I really think we stand a good chance to win it,” he told TimesLIVE. On the venue, he added: “But maybe Durban is home away from home because we used to play there. So it is what it is.”
The two sides drew 0-0 at Chatsworth in the league on 1 September, Durban City’s match centre shows. Stellenbosch are seventh.
The bottom line
Three bruised or weary giants at home, a newcomer with nothing to lose and a Durban reunion. Little-fancied Magesi won this trophy in 2024 by beating Sundowns 2-1 in the final, EWN and TimesLIVE recorded. The record backs Hunt’s point. By Wednesday night, we will know which of these clubs believes him.
Frequently asked questions
When are the knockout cup last 16 matches on Tuesday?
Orlando Pirates v Milford, Kaizer Chiefs v TS Galaxy and Mamelodi Sundowns v Marumo Gallants all kick off at 19:00 SAST on Tuesday 27 October 2026, the PSL confirms. Durban City v Stellenbosch is on Wednesday 28 October at 19:00 SAST.
Where is Orlando Pirates v Milford being played?
At Orlando Stadium in Soweto on Tuesday 27 October, kick-off 19:00 SAST. Pirates beat Milford 2-0 at the same ground on the opening day of the league season, 1 August.
Who are the defending champions of the knockout cup?
Orlando Pirates. They beat Marumo Gallants 2-0 in last year’s final in Mbombela. Stellenbosch won the first edition in 2023 and Magesi the second in 2024.
Who is Durban City’s coach for the Stellenbosch game?
Eric Tinkler, whom the club names as its head coach. Durban City announced him on 8 October.
Which teams are already in the knockout cup quarter-finals?
Golden Arrows and Siwelele, who won on Saturday 24 October, and AmaZulu and Sekhukhune United, who won on Sunday 25 October. The other four places are settled on Tuesday and Wednesday.