Richards Bay secured a famous victory when they defeated Kaizer Chiefs 2-1 in the Nedbank Cup Last 32 match which was played at FNB Stadium on Sunday evening.
Goals from Thabani Dube and Siyabonga Vilane handed the Natal Rich Boys the victory on the day, while Leonardo Castro netted for Amakhosi.
Amakhosi were keen to avoid an upset in the South African FA Cup after suffering a 2-1 defeat to their arch-rivals Orlando Pirates in a PSL match last weekend.
Bernard Parker, Siphelele Ntshangase and Happy Mashiane were among the players, who were making their return to the starting line-up as coach Gavin Hunt made six changes to the starting line-up which faced Pirates.
On the other hand, the Natal Rich Boys were looking to make it three wins in a row having hammered Bizana Pondo Chiefs 4-1 in the National First Division (NFD) match last weekend.
Dube, who started for TS Galaxy as they stunned Chiefs 1-0 in the 2019 Nedbank Cup final, was deployed in central defence by coach Simo Dladla, while former AmaZulu striker Somali Ntsundawana led the attack.
Richards Bay adopted a defensive approach as they sat back and they allowed Chiefs to dominate the match, but the hosts could not turn possession into clear goalscoring opportunities.
Amakhosi launched most of their attacks down the left-hand side through Mashiane, but the youngster's crosses were poor as they were either caught by goalkeeper Malcolm Jacobs or cleared away from danger.
The Natal Rich Boys were awarded a corner-kick following a rare attack by the visitors and they managed to open the scoring through their towering centre back Dube.
Khanyiso Mayo's curling corner-kick was headed home by Dube to make it 1-0 to Richards Bay from close range a minute before the half-hour mark after Akpeyi had failed to gather the ball.
Chiefs nearly responded with a goal at the other end when Ntshangase played a low cross for Samir Nurkovic, who was brilliantly denied by Jacobs at the near-post.
Parker's attempt was then blocked on the goal line by Dube and the visitors were able to contain Amakhosi and the score was 1-0 to Richards Bay at the interval.
Hunt made four changes prior to the start of the second-half as he introduced Lebogang Manyama, Leonardo Castro, Dumisani Zuma and Njabulo Blom.
Chiefs piled pressure on Richards' Bays' defence and Nurkovic's headed effort was saved on the goal-line by Jacobs and Katlego Mphatlhe cleared the ball away from danger.
Things went from bad to worse for Amakhosi as they were reduced to 10 players after Siphosakhe Ntiya-Ntiya was sent off having received his second yellow card of the game.
However, the Soweto giants continued to attack despite being numerically disadvantaged and they did level matters when Castro scored with a volley to make it 1-1 with 15 minutes left.
Amakhosi then had two clear chances which they failed to convert as Manyama's scuffed shot was easily saved by Jacobs, before Castro headed over the crossbar from close range.
The hosts were left to rue their missed chances as Vilane sealed Richards Bay's 2-1 win when he scored with a tap in after fellow second-half substitute Bayzel Goldstone's shot had hit the upright in stoppage time.
As a result, Richards Bay progressed to the Round of 16 for the first time since 2019, while Chiefs crashed out of the lucrative tournament.
Chiefs will now focus on their upcoming opening Caf Champions League Group C match against Moroccan against Wyad Casablanca which will be played on February 13.