Highlands made three changes from the MTN8 final loss as Ricardo Williams, Marks Munyai and Mlungisi Mbunjana entered with Siyabonga Zulu the visitors only marquee change.
Sphiwe Msimango almost headed the home side ahead after 12 minutes, but the effort went wide of Jonas Mendes goal following a cross into the area.
Both sides got a look in close to halftime, but the deadlocked remained locked as neither side rattled the back of the net drawing the half to a close in the process.
Changes from the bench following the restart happened on either side, with Reneilwe Letsholonyane introduced for Munyai while Karabo Tshepe replaced Tshwarelo Bereng.
Highlands wasted a big chance on 53 minutes when Peter Shalulile headed dismally off target after getting underneath a cross from Mokeke Mogaila.
Lidoda Duvha got a similar chance 12 minutes thereafter as Mwape Musonda opened space in the area from a low pass, but the Zambian dragged the effort wide from five metres.
The Lions of the North responded moments later when Shalulile got around the area following a through ball, but the visitors thwarted the danger.
Leopards fluffed another chance when Lesedi Kapinga dragged wide of the far corner after being sent clear from the defence 73 minutes gone.
Highlands found big chances to steal the win late on, but the home side proved wasteful upfront as the match went to extra time.
Leopards were brought to ten-man after Khuliso Mudau received a second yellow card for a studs up challenge, but Highlands didn’t utilise the extra man sending the match to a penalty shootout.
Neither side slipped up in the first five spot kicks of the shootout, however a miss from Leopards in sudden death allowed Msimango to slot home the winning kick.
Leopards: Mendes, Madau, Zulu, Katjiukua, Masia, Mokoena, Andrianarimanana, Phala, Musonda, Bereng, Kapinga
Subs: Muleka, A. Zulu, Ndou, Abubakar, Tshepe, Malajila, Ndlovu.