Mamelodi Sundowns have been eliminated from the Carling Knockout following a 7-6 shootout loss to Marumo Gallants after a goalless draw in both the regulation and extra time in the Round of 16 fixture played on Saturday in Pretoria.
Last season, Masandawana went all the way to the finals but were undone by surprise package Magesi FC who won 2-1 to become the first ever team to win a major title after making debut in Mzansi's top-flight football.
Furthermore, despite their dominance in the Premier Soccer League, the Brazilians have struggled to win cup competitions.
Interestingly, Sundowns and Gallants met in the semi-final of the previous edition whereby the former advanced owing to their 2-0 victory.
Frustrating first-half for Sundowns
Gallants looked happy to sit back and rely on counter attack against the defending PSL champions.
Portuguese import Nuno Santos had a massive chance to find the target after being set up by Khuliso Mudau. He, however, couldn't keep his shot down.
Tashreeq Matthews, who has been in a good form for Miguel Cardoso's men, came close in the 25th minute but his effort flew wide off the mark with the defenders beaten.
In the 43rd minute, Iqraam Rayners felt he was fouled in the 18-yard area by Mpho Chabatsane but the referee wasn't interested with calls for a penalty.
Reisinho receives a red card welcome!
Masandawana looked lively after the break in their quest to break the deadlock; in the 48th minute, the unmarked Mudau could have done better when he was fed the ball, unamrked in the 12-yard area but went for power and missed the target.
A few moments later, Arthur Sales was left unmarked just outside the area, but his well-taken shot missed the targe by inches following a slight deflection by a Gallants defender.
Substitute Teboho Mokoena thought he had done enough in the 81st minute when he beat the defenders to a cormer ball, but the Bafana Bafana Bafana international was denied by the crossbar.
New signing Reisinho lasted about five minutes after debut before getting his matching orders for a career-threatening foul on Siyabonga Nhlapo. The midfielder joined Masandawana recently as a free agent, signing a two-year contract with the club.
Gallants send Sundowns packing
Sundowns had to do the 30 minutes with 10 men, but still Gallants couldn't find the way past them.
In the shootout, Gallants won 7-6; they scored through Simo Mbhele, Agnikoi Eroine, Msendami, Mpho Chabatsane, Khumbulani Ncube, Siyabonga Nhlapo, and Washington Arubi, while Jaison Clifford and Kamohelo Sithole's strikes were saved by Ronwen Williams.
Aubrey Modiba, Peter Shalulile, Nuno Santos, Teboho Mokoena, Thapelo Morena and Malibongwe Khoza found the back of the net, but Arubi stopped strikes from Marcelo Allende, Fawaaz Basadien, and Mosa Lebusa.
Durban City became the first team to make the quarter-final after beating Polokwane City 4-1. On Saturday, Orlando Pirates also made it into the last eight thanks to a hard-fought 1-0 win over Siwelele.
The other two teams in the quarters are TS Galaxy who beat Orbit college by a solitary goal, alongside Golden Arrows who were 3-1 winners over Sekhukhune United.