Orlando Pirates Face Milford in Carling Knockout Before Soweto Derby Against Kaizer Chiefs

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October 27, 2026

Orlando Pirates play Milford FC in the Carling Knockout last 16 on Tuesday. The cup match comes just days before the Soweto Derby against Kaizer Chiefs.

Pirates are the defending champions of the Carling Knockout. They won the trophy last season and need a win against Milford to keep their title defence alive.

A win on Tuesday would send the Buccaneers into the quarter-finals of the competition.

The busy week follows Pirates’ return to the CAF Champions League group stages. The club secured its place in the group stages after its recent qualifiers.

Reaching the group stages was an important step for coach Abdeslam Ouaddou, IOL reported. His team missed out on the group stages last season.

Milford are a KwaZulu-Natal side. IOL reported that they will be keen to make their mark against one of the biggest clubs in South Africa.

A knockout cup tie leaves Pirates little room for error. Ouaddou will have to manage his squad while making sure his team avoids an upset, according to IOL.

After the Milford match, Pirates turn to the Betway Premiership. They meet Kaizer Chiefs at FNB Stadium in Soweto on Saturday.

The Soweto Derby is one of the biggest matches on the South African football calendar. Bragging rights and league points will be on the line.

IOL reported that Pirates will hope to carry the confidence from their Champions League campaign into the derby.

The tight schedule is expected to test the depth of the squad. Players will also need to recover from the physical and emotional demands of the Champions League qualifiers.

Ouaddou has spoken about the importance of having enough attacking players to rotate. He said this matters because Pirates are competing on several fronts.

The coach will need players from his wider squad to step up during this run of games, IOL reported.

Pirates face three important matches in this stretch. The run ends with the derby, and the club will look to keep its momentum going in both local and continental football.

A win over Milford would keep one trophy within reach. It would also let Pirates go into the Soweto Derby with their cup hopes still alive.

The match against Milford FC takes place on Tuesday, with the Soweto Derby against Kaizer Chiefs at FNB Stadium following on Saturday.

Source: this article is based on reporting by IOL Sport. Image: IOL Sport. Written with the help of AI and published by the Tzaneen Voice Sports desk. See our Editorial Standards.