The draw also produced a KwaZulu-Natal derby between Richards Bay FC and AmaZulu FC.
Orlando Pirates and Mamelodi Sundowns avoided each other in the draw for the last 16 round of the Nedbank Cup.
The draw was conducted at the SuperSport studios in Randburg, Johannesburg on Wednesday.
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Pirates, who have reached the final in each of the past three seasons, winning the first two before finishing runners-up last year against their rivals Kaizer Chiefs, are at home to Motsepe Foundation Championship title contenders Casric Stars.
Sundowns, who were knocked out by eventual champions Chiefs in the semifinals last season, are away to TS Galaxy.
The draw also produced a KwaZulu-Natal derby between Richards Bay FC and AmaZulu FC.
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The dates, times and venues for the round of 16 will be announced by the Premier Soccer League at a later stage, but the fixtures are likely to be played on the weekend of 21-22 February.
The full Nedbank Cup last 16 draw:
Milford FC vs Mkhambathi FC
Golden Arrows vs Stellenbosch FC
AmaTuks vs Sekhukhune United
Jacksa Spears vs Vasco Da Gama
TS Galaxy vs Mamelodi Sundowns
Upington City vs Durban City
Richards Bay vs AmaZulu
Orlando Pirates vs Casric Stars
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