Pule Maraisane and Waseem Isaacs led the line for All Stars, while former SuperSport United duo Thabiso Nkoana and Atusaye Nyondo did duty for the Tshwane outfit.
All Stars looked to hit the front from the first few exchanges following a free-kick, but goalkeeper Itumeleng Lesu made a fantastic double save before Nkoana threatened at the other end.
However, All Stars regained momentum minutes from the half-hour mark and hit the front after Isaacs beat Lesu to a ball over the top before slotting into an empty net.
The away side started the second half quite confident, as a snap-shot from a tight angle by Nyondo cannoned off the side-netting with the host on the back-foot.
Callies rang the changes ten minutes from the restart in Pogiso Mahlangu, who came on for Nkoana as Edwin Sitayitayi entered ahead of Nyondo.
Mahlangu made the desired impact midway in the second half when he found space in the centre of the area to head home a cross from the right-side.
The joy lasted just two minutes after Maraisane showed sharp reactions to a free-kick to head into the far corner of the net.
Callies steadied ground a minute to go and levelled with a shot from a tight angle by Sitayitayi following a throw-in from Thabo Moloi, as extra-time followed.
Sitayitayi could've had a brace right inside extra-time, but found the crossbar before the woodwork denied Njabulo Buthelezi too, whilst Aupa Moeketsi saw red for a foul as penalties followed.
A drama-filled shoot-out saw both sides miss two of their five kicks to force a sudden-death, which Callies clinched after Keorapetse Sebone converted the winning kick.