Richards Bay upset Kaizer Chiefs but Swallows, Chippa United and Black Leopards were able to get past their GladAfrica Championship opponents to reach the Nedbank Cup last 16.
Swallows 1-0 Cape United
Swallows moved into the last 16 with a narrow 1-0 win over a competitive Cape United.
Roger De Sa’s GladAfrica Championship team from Cape Town put in a good performance against high-flying Swallows, but eventually Swallows’ individual excellence came through.
The Dube Birds went into the lead in the 57th minute, when former SuperSport United midfielder Kamohelo Mahlatsi got the goal that proved to be the winner.
Chippa United P 2(4)-2(3) Free State Stars
Another DStv Premiership almost fell to a GladAfrica Championship side, but Chippa fought back to beat Free State Stars 4-3 in a penalty shootout.
Namibian Riaan Hanamub grabbing the lead in the 85th minute after a good assist from Ayabulela Konqobe.
But the lead was short-lived as Ea Lla Koto found the equaliser through Abdul Suanon two minutes later, and the game went to extra time.
The visitors took the lead through Rankoko Tau near the end of first half of extra time.
Four minutes from time Andile Mbenyane levelled matters again for Chippa and the match went to penalties.
Chippa prevailed in the shootout as they were successful with four of their spot kicks, while Stars were only able to convert three.
Jomo Cosmos 1-2 Black Leopards
A tough battle between two old rivals. For most of the game they looked evenly matched, but in the end Leopards prevailed 2-1 over Cosmos.
Finally in the 82nd minute Ovidy Karuru scored the opening goal, doing well to turn in the box, and finishing under the keeper.
But that lead didn’t last long and Khethukuthula Zwane grabbed an equaliser a minute later, finishing from just inside the box.
Karuru though grabbed the winner in the 88th minute, as the Zimbabwean headed in from a corner.
Kaizer Chiefs 1-2 Richards Bay
Richards Bay caused the upset of the round of 32, when they beat Chiefs 2-1 at the FNB Stadium
While Chiefs controlled the possession, their GladAfrica opponents did not seem over-awed in the first half, creating a few chances on the counter.
And it was Richards Bay who took the lead through Austin Dube in the 29th minute, as he took advantage after Daniel Akpeyi missed a punch, and headed in from a corner.
Malcolm Jacobs made a good save in the 54th minute to deny Samir Nurkovic as Chiefs pushed hard for an equaliser.
It got worse for Chiefs, as they were down to ten men in the 64th minute after Siphosakhe Ntiya-Ntiya picked up a second yellow card for a foul on Katlego Maphathe.
But the ten men of Chiefs found the equaliser in the 77th minute, Leonardo Castro improvising and scoring off the ground to beat Jacobs.
Simo Dladla’s men grabbed the winner in the 90th minute, Bayzel Goldstone’s initial shot hit the woodwork and Siyabonge Vilane followed up to tap in.