Ten-man Kaizer Chiefs suffered a shock 2-1 defeat and elimination from the Nedbank Cup by GladAfrica Championship side Richards Bay on Sunday.
Thabani Dube opened the scoring with a deft header at the FNB Stadium on 29 minutes.
Siphosakhe Ntiya-Ntiya was dismissed for a second yellow card on 64 minutes, but Amakosi substitute Leonardo Castro found a leveller with 77 minutes played.
And with the game seemingly headed for extra time, Richards Bay substitute Siyabonga Vilane popped up with the winner in the first minte of injury time, to secure his side's place in the last 16.
Chiefs started this match on the front foot but the Natal Rich Boyz showed some good attacking promise in the opening exchanges.
Lindokuhle Mthembu tested Daniel Akpeyi with a volley on nine minutes that didn't test the Chiefs' stopper while Victor Bakah fired over the target from a long way out with 13 minutes played.
Chiefs though were beginning to string some passes together as they began to impose themselves on their opponents.
Samir Nurkovic was just offside with a header he glanced wide, and while the hosts retained much of the possession, it was the away side who looked the more threatening
Dube took his chance as he scored with a deft close-range header from a superb corner from the right from Khanyisa Mayo, that left Akpeyi with no chance.
Chiefs were almost immediately level from the restart but Bay keeper Malcolm Jacobs made a superb save to deny Nurkovic from close range.
Mayo fired in at Akpeyi moments later, but the keeper was equal to the effort ahead of a flurry of set-pieces from Richards Bay that were ultimately dealt with.
Akpeyi was under pressure from another good corner delivery from Mayo that so nearly snuck under the crossbar.
Chiefs' attacks were limited to balls in from wide positions, while Jacobs comfortably dealt with a long-range effort from Bernard Parker.
Nkosingiphile Ngcobo flashed his 45th minute shot from the edge of the 18-yard area off target, as Chiefs looked to end the first half strongly.
Not willing to risk elimination, Gavin Hunt made four changes at half-time, with Dumisani Zuma on for Happy Mashiane, Njabulo Blom on for Darrel Matsheke, as Leonardo Castro replaced Parker and Lebogang Manyama took over from Siphelele Ntshangase.
Nurkovic had the ball in the back of the net on 49 minutes but was correctly ruled to have been in an offside position.
Lwandile Mabuya replaced Mayo and Thabo Maphakisa came on for Franklin Ogbonna for Richard's Bay with 52 mintes on the clock.
Jacobs made a sensational one-handed save low to his right from a point-blank Nurkovic header, while it was the Serbian who remained Chiefs' main goal-threat, as he fired wide after creating space for himself on the hour mark.
But it went from bad to worse for Kaizer Chiefs after Ntiya-Ntiya was shown a second yellow card, for clipping Katlego Maphathe on 64 minutes on the half-way line as he raced forward.
Bakah was off target with shot from range, as Chiefs made one final change, in replacing Ncgobo with Reeve Frosler.
Richard's Bay came close to a second goal but there was no one on the end of a super ball across the face of the Chiefs' goal with Agpeyi stranded.
Vilane and Bayzel Goldstone came on for Somila Ntsundwana and Mthembu for Richards Bay with 16 minutes of the match remaning in a bid to see out the tie, with some fresh legs.
Chiefs upped the ante in search of an equaliser and were finally rewarded in the 77th minute.
Zuma's ball into the box from the left was controlled by Chiefs substitute Castro, and just as the ball looked to get away from him, he swung his boot - while on the ground - and found the back of the net.
Mapakisa was off-target on the volley in a let off for Chiefs, with time winding down, before Manyana failed to beat Jacobs with a mis-hit shot at the other end.
Nurkovic should have done better on 83 minutes but couldn't keep his shot down, as Castro headed over from just in front of the goalline.
And despite continuing to threaten, it was Richards Bay who won it in stoppage time to shock their hosts and secure their place in the last 16 of this illustrious opponents.
Goldstone beat Agpeyi but not the right upright, but the ball fell kindly for Vilane to tapped home the all-important winner.
- TEAMtalk media