Both Casric Stars and Milford are hoping to become the fifth and possibly sixth second-tier side to reach the Nedbank Cup final since 2008.
Mpumalanga Black Aces (2008), University of Pretoria (2009), Black Leopards (2011) and TS Galaxy (2019) are the others, with the latter the only side to have lifted the trophy when they beat Kaizer Chiefs 1-0 in the decider in Durban.
It is going to be a tough assignment for both Casric and Milford, however, as they are away to top-flight opposition.
Durban City host Casric Stars at Chatsworth Stadium on Saturday, 4 April (kick-off 3pm and live on SuperSport), while Milford travel to Solomon Mahlangu Stadium a day later to meet TS Galaxy (3pm and live on SuperSport).
In 2008, Mamelodi Sundowns beat Aces in the final at the Johannesburg Stadium. It took a Lerato Chabangu goal three minutes from time to separate the teams as Black Aces threatened an upset with an excellent display in the decider.
Can Milford emulate TS Galaxy's historic #NedbankCup feat from 2019?
— SuperSport Football ⚽️ (@SSFootball) April 1, 2026
The head coach, Xhanti Phuphuma, says this weekend's semi-final is a step closer to a dream they want to achieve.#SSDiski pic.twitter.com/PhQcjx4oBI
The next year, for the second year running, a side from the National First Division made the final of the Nedbank Cup but again fell just short.
AmaTuks had a thrilling run on their way to a meeting with Moroka Swallows at the Rand Stadium in the decider. But they would lose 1-0 after a goal from the Birds’ Brazilian centre back Vinicius Da Silva.
The 2011 Nedbank Cup will forever be remembered for the run of then third-tier side Baroka to the semifinals, but it was Orlando Pirates who lifted the trophy.
Pirates defeated second-tier Black Leopards 3-1 in the decider after falling behind to a Rooi Mahamutsa own goal. Isaac Chansa restored parity before a brace from Thulasizwe Mbuyane sealed the win for the Buccaneers.
In 2019, second-tier TS Galaxy shocked South African football as they became the first club from outside the top flight to lift the trophy, defeating fancied Kaizer Chiefs 1-0 in the decider in Durban.
The game looked as though it was headed for extra time before Zakhele Lepasa converted a late penalty for Galaxy to spark wild scenes of celebrations for the history-making Rockets.