Stars edged AmaZulu 2-1 after extra time of their encounter in Durban, while Milford beat Sekhukhune United 3-2 on penalties after the teams played to a 2-2 draw.
It is rare, but not unheard of, for two lower-league sides to reach the semi-finals. In 2011, second-tier Black Leopards met third-tier Baroka FC in the last four.
Stars’ upset came in the same stadium where second-tier TS Galaxy stunned Kaizer Chiefs in the final in 2019 to become the only team from that division to lift the trophy.
Stars had to weather an early storm from AmaZulu but took the lead on 12 minutes.
Having cleared from their own box, Stars were quickly on the break and when Leletu Skelem was played into space on the left wing, he drove towards the box and played in Mfundo Thikazi to provide a neat left-footed finish into the bottom corner of the net.
Remarkably, it is Thikazi’s first goal since he scored for Royal AM at Chippa United in August 2023.
Pule Ekstein found an equaliser on 49 minutes after he beat the offside trap and side-footed into the back of the net for his second goal of the campaign and six overall in his Nedbank Cup career.
It looked as though the game might go to penalties until Decide Chauke came up with the winner on 115 minutes. His low shot across goal struck the far post and then trickled agonisingly along the goal line before going in.
Milford FC took an early lead against Sekhukhune United when Cheswyn Philander scored inside four minutes as he was left in acres of space on the right-hand side of the box and side-footed into the goal.
But Sekhukhune turned the game around as Bradley Mojela scored just a few minutes later when he rose highest to meet the ball with a header.
That was how it stayed until extra time, when Sekhukhune took the lead as Olerato Mandi was left unmarked at the back post and fired into the net for his first goal for the club since his arrival from Pretoria Callies at the start of the season.
But Milford did not lie down and they found an equaliser on 115 minutes as Sibulele Mekuto headed into the back of the net from a free-kick to take the game to penalties.
Sekhukhune missed three times in the shoot-out and it was Milford goalkeeper Siphamandla Hleza who scored the winning penalty to take his side through.
It will be the first time in the semi-finals for both Stars and Milford.
Sunday sees Galaxy host third-tier Jacksa Spears and Lamontville Golden Arrows welcome Durban City in the other two quarter-finals. The draw for the last-4 will be on Monday night.
