Buoyed by their midweek victory over Stellenbosch FC in the DStv Premiership, the Buccaneers called on the heavy artillery with striker Tshegofatso Mabasa restored to the line-up.
It was the host that showed the first promise seven minutes gone when Kelvin Nokuwa closed-in with a low shot from a decent area which goalkeeper Siyabonga Mpontshane gathered.
The Buccaneers didn't lie down but stood forth near the half-hour mark and watched Linda Mntambo feed Terrence Dzvukamanja, who went and cracked the upright.
Oilers regained momentum towards halftime and brought Randy Dukuly into space to hit the side-netting from a clever ball as the Buccaneers went to sleep in defence.
More nerves followed the Sea Robbers as Oilers got a penalty five minutes to halftime following a hand ball in the area, but Ebenezer Solo missed the resultant spot-kick.
However, the Buccaneers had the front-foot inside 43 minutes through a well thought finish from Mabasa with the host caught napping.
Oilers entered the second half desperately looking to draw level, but Mpontshane was up to the task as Bucs introduced Bongani Sam off the bench for Dzvukamanja.
The Sea Robbers remained on guard following the middle of the second half and watched Mpontshane produce another solid block off Brandon Debah's plight.
Although, it was all Pirates inside the closing exchanges with Gabadinho Mhango closing in with a free-kick seconds from entering off the bench.
The final say inevitably belonged to the Buccaneers as Fortune Makaringe entered the area in added time to go on and head home Sam's peach delivery, seeing the Soweto giants to a first-leg victory.
Orlando Pirates: Mpontshane, Nyauza, Mngonyama, Mabaso, Mako, Motshwari, Makaringe, Hotto, Mntambo, Dzvukamanja, Mabasa.
Subs: Sandilands, Shandu, Maela, Sam, Monare, Makgaka, Mhango