Defending Nedbank Cup champions Mamelodi Sundowns booked their spot in the last-16 with a 3-2 win over Stellenbosch FC at Loftus Versfeld Stadium.
Peter Shalulile scored what proved to be the winner in the 117th minute of the match.
Goals from Shalulile and Gaston Sirino set the Brazilians on course for victory in regulation time following Ashley du Preez's opener, but Phathutshedzo Nange scored a 93rd-minute equaliser to level matters and set up an additional 30 minutes of extra-time.
Stellies got off to the perfect start as they broke the deadlock just 12 minutes into the match following a mistake by Rivaldo Coetzee, whose poor pass was intercepted by Du Preez.
Du Preez then pounced and outpaced his marker Mosa Lebusa, before firing past oncoming Ricardo Goss with a low shot to make it 1-0 to Stellenbosch.
Parity was restored in the 16th minute when Lebohang Maboe's long ball found Shalulile, who controlled it brilliantly before hitting the back of the net to make it 1-1.
Sundowns would have been bemused to go to the break at 1-1, creating chances, hitting the post, and conceding a soft opener.
Lyle Lakay’s stray pass deep in his half to the feet of Du Preez allowed the 23-year-old to run between the centrebacks unchallenged and finish low past Goss.
Lakay’s free-kick in first-half added time was palmed by Shane Stephens onto the upright.
Sirino thought he had grabbed a late winning goal when he beat Stephens with a hard and low shot which sneaked into the bottom right corner to make it 2-1 to Sundowns a minute into stoppage time.
However, Nange had other ideas as the 29-year-old turned home subsitute Junior Mendieta's cross three minutes into stoppage time to ensure that the game ended in a 2-2 draw in regulation time and extra-time followed.
A game headed for penalties had a plot twist left before that. In the 27th minute of extra time Downs scored from another appropriately efficient passing display, Sirino on the left finding Zwane outside the box to thread through to Shalulile, who struck an emphatic winner past Stephens.
Stellenbosch had one last chance to send the match to penalties but Goss was alert to the danger and produced a fine save to keep out Nathan Sinkala's header attempt as Sundowns held on to book their spot in the next round where they join Polokwane City, who defeated fellow GladAfrica Championship side Steenberg United 2-0 in the Limpopo province earlier in the afternoon.
Sundowns will now take on Sudanese giants Al Hilal Omdurman in their opening Caf Champions League Group B match on February 13 and Stellies are set to face Lamontville Golden Arrows in a PSL game on February 12.
Mamelodi Sundowns (1) 3 (Shalulile 16' 117' Sirino 90+1')
Stellenbosch FC (1) 2 (Du Preez 12' Nange 90+3')
Sundowns 3-2 after extra-time
Mamelodi Sundowns: Goss, Lakay, Nascimento (Erasmus 87'), Lebusa, Maboe, Coetzee, Jali, Mkhulise (Morena 109'), Sirino, Zwane (Kapinga 87'), Shalulile (Soumahoro 120').
Stellenbosch FC: Stephens; Van Heerden, Robertson, Johannes, Macheke (Moon 112'), Sinkala, Msengi (Nange 68'), Adams (Scott 90'), Van Rooyen (Mthethwa 75'), Dimgba (Mendieta 67'), Du Preez (Skelem 46').