Kaizer Chiefs have advanced to the Last 8 of this year's Telkom Knockout Cup in a nail-biting encounter against Cape Town City at Cape Town Stadium.
Kermit Erasmus opened the scoring for the home side but a late Samir Nurkovic goal took the game to extra time.
Amakhosi converted four of their five penalties with Lebogang Manyama missing his spot-kick while Daniel Akpeyi made a save to help his team progress.
Ernst Middendorp welcomed Reeve Frosler back from an injury lay-off and the full-back walked straight into the starting line-up alongside Erick Mathoho, who was away with Bafana Bafana last weekend.
Leonardo Castro started ahead of Samir Nurkovic after scoring a first-half hat-trick against Mamelodi Sundowns.
Amakhosi lined up in a 3-4-3 formation with Frosler playing in a more advanced role on the right-hand side.
The Citizens fielded their strongest possible line-up with Erasmus leading the attack alongside the likes of Mark Mayambela and Surprise Ralani.
After a frantic start into the first period which saw both sides go neck-on-neck on each other, Chiefs received a penalty in the 28th minute after Taariq Fielies was adjudged to have handled the ball inside the box.
Daniel Cardoso stepped up but ballooned his spot-kick, much to the disappointment of the Amakhosi fans out in the stands.
The miss sprung Cape Town City to life and it didn't come as a surprise to see Erasmus open the scoring with a stunning finish from outside the box to silence thousands of Chiefs fans inside the venue.
Chiefs lost Kearyn Baccus through an injury soon after City's goal and the midfielder was replaced by George Maluleka.
Bernard Parker was a second casualty as he had to be stretchered off four minutes from the interval, and his place was taken by Nurkovic with the armband handed to Maluleka.
In the end, City went into the half-time break with their tails up. Middendorp's half-time talk appeared to help Chiefs as they came out guns blazing from the dressing rooms.
The visitors should have levelled matters minutes into the second half but Maluleka fluffed his attempt over the top.
Akpeyi proved just why Middendorp rates highly as he produced three saves in quick succession to keep the scoreline respectable.
Cape Town City gave Chiefs a scare in the 68th minute as Makola rattled the crossbar with Akpeyi well-beaten.
Peter Leeuwenburgh was not to be outdone by Akpeyi as he did the most to keep Dumisani Zuma at bay three minutes later.
With the encounter seemingly done and dusted, Nurkovic fired home a half-volley which proved too strong for Leeuwenburgh as the match went to extra time.
Neither side could find the back of the net in extra time and the encounter had to be settled on penalties.
City failed to convert two of their four penalties kicked, with Akpeyi making a fine save to deny Ebrahim Seedat before Fielies fired wide to hand Chiefs the advantage.
Manyama was denied by Leeuwenburgh but Mathoho scored the winner as Chiefs won 4-2 on penalties.