Tshakhuma Tsha Madzivhandila secured a 4-3 victory over fellow PSL side Swallows FC on penalties following a 2-2 draw at Peter Mokaba Stadium in Polokwane.
Thabo Mnyamane opened the scoring just 18 minutes into the match as he netted his second goal in this season's Nedbank Cup.
The former SuperSport United forward beat Swallows goalkeeper Virgil Vries with a well-taken free-kick to make it 1-0 to Tshakhuma.
The Beautiful Birds were able to level matters through Sipho Sibiya after the Vhadau Vha Damani defence was exposed on the stroke of half-time.
Joseph Mhlongo set-up Sibiya, who headed past Washington Arubi to make it 1-1 heading into the half-time break - scoring his second goal of the campaign in the process.
It took just seven minutes for the hosts to restore their lead through Rhulani Manzini, who ended his six-match goal drought.
Mogakolodi Ngele was the provider as the Botswana international's cross was headed home by Manzini to make it 2-1 to Tshakhuma.
The goal did not deter the Beautiful Birds as they launched attacks and they managed to restore parity through Vuyo Mere.
The ball fell kindly for Mere in the box and he fired past Arubi to make it 2-2 in the 75th minute to ensure that the game ended in a draw in regulation time.
There were no goals in extra-time with Vries denying Meshack Maphangule from the penalty spot after Joseph Molangoane was fouled in the box in the 104th minute.
Tshakhuma went on to win 4-3 on penalties with Arubi denying Musa Nyatama from the last penalty kick and Vhadau Vha Damani advanced to the quarter-finals.
Meanwhile, Cape Town All Stars claimed a 5-3 win over their National First Division rivals Cape Town Spurs on penalties following a 3-3 draw at Parow Park Stadium in Cape Town.
The first goal of the match was netted by Waseem Isaacs in the 17th minute as the former Stellenbosch FC striker scored his fourth goal of the season to make it 1-0 to All Stars.
Spurs fought back and piled the pressure on Igugu Lekapa, whose defender Thabo Mokhele scored an own-goal to make it 1-1 in the 62nd minute.
The encounter ended in a draw in regulation time and extra-time followed with Junior Batista handing Spurs a 2-1 lead eight minutes into the first-half of extra-time.
However, Zaahir Witbooi levelled matters for Igugu Lekapa to make it 2-2 in the 111th minute, but Igor de Oliveira restored Spurs' lead to make it 3-2 to the visitors a minute later.
The match ended in a 3-3 draw after Ronaldo Maarman snatched a late goal with 11 minutes left in the second-half of extra time and the game went into a penalty shootout.
All Stars went on to secure a 5-3 victory on penalties with Thabo Moloisane converting the last spot-kick for the hosts.
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