Amakhosi ended 10 years without a trophy when they overcame Orlando Pirates 2-1 to lift the 2025 Nedbank Cup final.
They have been paired with a struggling Stellies side now under the guidance of former Chiefs head coach Gavin Hunt after Steve Barker's exit.
Under Nasreddine Nabi, Chiefs side beat Stellies in the quarter-finals and also beat the Cape Winelands club home and away in the Betway Premiership last season.
They did, however, lose to Barker's team on penalties in the last 16 of the Carling Knockout this season.
Other ties see Mamelodi Sundowns host Motsepe Foundation Championship side Gomora United as Orlando Pirates are away to Tshakhuma Tsha Madzivhandila, while Premiership sides Durban City and Chippa United square up as Marumo Gallants travel to take on TS Galaxy.
Full Nedbank Cup last 32 draw
Stellenbosch FC v Kaizer Chiefs
Army Rockets v Casric Stars
Hungry Lions v University of Pretoria
Tshakhuma Tsha Madzivhandila v Orlando Pirates
Durban City v Chippa United
Polokwane City v AmaZulu
SSU MI17 FC v Milford FC
SAFA Western Cape v Luthuli Brigades FC
FC Cardinals v Jacksa Spears
Mkhambathi FC v Lerumo Lions
Upington City v Magesi FC
Highbury FC v Sekhukhune United
Golden Arrows v Orbit College
Mamelodi Sundowns v Gomora United
TS Galaxy v Marumo Gallants
Siwelele FC v Richards Bay FC
Kaizer Chiefs duo Manqoba Ozoemena and Ofentse Kgosana are reportedly set to spend the rest of the 2025/26 Motsepe Foundation Championship on loan at Casric Stars.
Former Kaizer Chiefs goalkeeper Brian Baloyi insists something needs to be done address the declining number of South African goalkeepers in the Betway Premiership.
Kaizer Chiefs have sent talented DStv Diski Challenge defender Bobo Sima out on loan to Mochudi Centre Chiefs.
Kaizer Chiefs began 2026 on a winning note in the DStv Challenge, cruising to a convincing 4-0 victory over Richards Bay at Mpumalanga Stadium this past weekend.
