Fourteen of the 16 teams who will be in the draw for the second round are now known, with two more Last 32 matches to be played on Tuesday.
Siwelele took the lead in Bloemfontein as Grant Margeman scored inside 19 minutes, his first goal since netting for SuperSport United against Stellenbosch in August 2023.
But Richards Bay equalised through Sbangani Zulu deep into the second half to force the game into extra-time, before eventually winning it in the additional half-hour.
Lundi Mahala scored twice within the first seven minutes of extra-time to put Richards Bay in control, but Siwelele made a fight of it and forced an own goal from Thabani Zuke before Siphelele Luthuli equalised.
That sent the match to a penalty shoot-out, and it was the visitors who held their nerve to advance.
Mkhambathi ensured they would be the third team from the ABC Motsepe League into the Last 16, joining CR Vasco da Gama and Jacka Spears.
Mkhambathi defeated second-tier Lerumo Lions 2-1 at the Sugar Ray Xulu Stadium, with their winning goal coming in the 89th minute from Xolani Zondo.
Mehluleli Ndelu had given the home side the lead, but they were pegged back when Ntuthuko Mlotshwa equalised for the Lions on 35 minutes. However, the KwaZulu-Natal side were able to hold on for a famous win.
The record number of amateur teams in the Nedbank Cup Last 16 is four, which has been achieved on two previous occasions. That mark will be matched this year if SSU M-17 FC defeat Milford FC in their Last 32 clash on Tuesday.
It was ‘take two’ for Lamontville Golden Arrows, who defeated Orbit College 3-0 on Sunday in a match that had been abandoned at the first attempt a day earlier due to lightning.
Golden Arrows led 1-0 when that game was called off at halftime, and they repeated the feat on Sunday afternoon, with Abafana Bes’thende again showing their dominance.
Angelo van Rooi gave Golden Arrows the lead midway through the first half before Sede Dion added a second on 33 minutes.
They added their third 11 minutes from the end as Ayabulela Maxwele made the scoreline more emphatic.
Golden Arrows had exited in five of the previous six seasons since reaching the semi-finals in 2019, making this a rare recent appearance in the draw for the Last 16.
The 2019 winners TS Galaxy advanced to the Last 16 after defeating 2021 champions Marumo Gallants 1-0 after extra-time at the Solomon Mahlangu Stadium.
It was a hard-fought contest that was ultimately settled by Victor Letsoalo’s strike after 104 minutes to send Galaxy through.
University of Pretoria also progressed to the Last 16 with a 5-4 penalty shoot-out victory over hosts Hungry Lions at the Mxolisi Dicky Jacobs Stadium after the sides played to a 1-1 draw.
The game was goalless after 90 minutes, but Bongumusa Nkosi gave AmaTuks the lead in the 104th minute. Yannick Angoume then equalised for the Lions with virtually the last kick of extra-time.
That sent the match to penalties, and when Parsley Fielies skied his effort over the crossbar, AmaTuks clinched the shoot-out.