Kaizer Chiefs were knocked out of the Nedbank Cup on penalties by Motsepe Foundation Championship side Milford.
Neither side was able to break the deadlock in the round of 32 clash on Sunday, before a missed Edson Castillo spot-kick condemned Chiefs to a 5-4 defeat.
A much-changed Amakhosi team took to the field at the FNB Stadium but it was regular starter Ashley Du Preez who looked lively early on as he scooped a strong effort onto the crossbar.
Chiefs continued to press and Edson Castillo produced a shot from close-range that required a goal-line clearance from the Milford defence.
Christian Saile came as close as anyone to finding the back of the net in the first half with a header that flew just over the target, as the opening stanza ended with Nkosingiphile Ngcobo forcing a fine low save from Siphamandla Hleza.
The Milford keeper was alert from the start of the second period as he got down well to deny Du Preez before pushing Mduduzi Shabalala’s rebound around his post.
Castillo was unable to direct his header from the resultant corner inside the back post, and Edmilson Dove was similarly wasteful with his effort with time winding down.
Chiefs substitute Ranga Chivaviro saw a curling strike palmed clear for the last real chance of the tie, leading the match into extra-time.
Milford were reduced to ten men when Vusumuzi Mthabela was dismissed with a second yellow, but the game ultimately went to penalties where all but one of the spot kicks were converted.