Orlando Pirates will face Milford FC in the Carling Knockout Round of 16 as they launch the defence of their League Cup title. The draw, conducted on Wednesday, sets up a first-ever cup meeting between the sides.

Milford FC are top-flight newcomers making their debut in the competition, adding a fresh challenge to Pirates' already demanding October schedule. The Buccaneers aim to go back-to-back in the Carling Knockout after their 2025/26 triumph ended a 14-year wait for the trophy.

This will be only the second meeting between the clubs, following a league season opener in August. The tie will be played at the Orlando Amstel Arena, with Pirates welcoming Milford to Es’godini.

Head coach Abdeslam Ouaddou acknowledged a sense of déjà vu as his side prepares for another title defence against a newly-promoted opponent. His team heads into the cup clash in strong league form, sitting second in the Premier Soccer League with 22 points from eight games. Their recent results show four wins from their last five outings.

Other Carling Knockout fixtures include Kruger United against AmaZulu FC and Golden Arrows versus Chippa United. Orlando Pirates will start their Carling Knockout defence against Milford FC at the Orlando Arena.

Further reading: orlandopiratesfc.com

The Premier Soccer League confirmed the Carling Knockout Round of 16 draw was conducted at the Langhams Lifestyle Estate in Johannesburg on Wednesday. The winners of the competition will face a PSL All Star XI, the league stated. Orlando Pirates head into the fixture with a league-leading defence, having conceded just one goal in eight games. The team's last result was a 3-0 win over TS Galaxy on October 13, with goals from Boitumelo Lawrence Radiopane, Tshepang Moremi and Simphiwe Masilela.

Head coach Abdeslam Ouaddou welcomed the home draw but warned Milford FC are a difficult challenge. "It's a very good team, well coached, very organised, disciplined," Ouaddou said. The Buccaneers head into the tie with a league-leading defence, having conceded just one goal in eight games. Their last result was a 3-0 win over TS Galaxy on October 13.