Three Last 16 matches were played on Sunday and two NFD clubs advanced to the next round
Chippa United emerged 2-1 winners over fellow PSL side Cape Town City in the Nedbank Cup Last 16 match which took place at Nelson Mandela Bay Stadium.
Augustine Chidi Kwem put the Chilli Boys in the lead three minutes before the half-hour mark with Maloisane Mokhele providing the assist.
Mokhele played a low pass to Kwem, who guided the ball into the bottom left corner to make it 1-0 to Chippa.
City were trailing 1-0 during the half-time break and they came back rejuvenated following their half-time team talk with coach Jan Olde Riekerink.
The Dutch tactician had made a triple substitution - introducing Justin Shonga, Keanu Cupido and Abdul Ajagun prior to the start of the second-half.
It was Ajagun who made an impact on the game in the 66th minute as the former Nigeria youth international scored on his debut for City to make it 1-1.
Ultimately, the match ended in a 1-1 draw in regulation time and the Chilli Boys went on to win the match in extra-time.
Bienvenu Eva Nga turned home a cross from his captain Andile Mbenyane to seal a 2-1 win to Chippa in the 116th minute.
Meanwhile, Richards Bay edged out their National First Division rivals TS Sporting 2-1 at Mbombela Stadium.
All three goals were scored in the second-half with Decide Chauke breaking the deadlock to make it 1-0 to Sporting in the 72nd minute.
However, the Natal Rich Boys were awarded a penalty four minutes later and Khanyiso Mayo hit the back of the net from the penalty spot to make it 1-1.
The two teams then pushed for the winning goal and it was Mayo who proved to be the hero for the Natal Rich Boys.
The former South Africa youth international beat Sporting goalkeeper Abram Ngcobo in the 86th minute to seal a 2-1 win to Richards Bay - completing his brace in the process.
Lastly, an encounter between Pretoria Callies and JDR Stars ended in a 0-0 draw in a clash between two NFD clubs at Lucas Moripe Stadium.
Callies went on to claim a 5-4 win on penalties and they joined eight-time Nedbank Cup winners, Orlando Pirates in the quarter-finals with the Soweto giants having defeated Maritzburg United on Saturday.