The Buccaneers were without captain and centreback Nkosinathi Sibisi, who was serving a one-match suspension, while Melusi Buthelezi started in goal ahead of Sipho Chaine, who was one match away from suspension.
The Natal Rich Boyz missed Justice Figareiro and Moses Mthembu.
Coach Jose Riveiro's Bucs made a lively start and the pressure paid off as Maswanganyi broke the deadlock with a shot on the edge of the box that looped away from goalkeeper Ian Otieno after he combined with Relebohile Mofokeng.
Maswanganyi completed his brace four minutes later as he combined with Mofokeng again to make it 2-0.
After scoring those two goals, Pirates were guilty of taking their foot off the pedal and allowing Bay to come at them, giving the KwaZulu-Natal chances to score.
Maswanganyi brace helps Orlando Pirates sink Richards Bay in Nedbank Cup
Image: Gerhard Duraan/Gallo Images
Orlando Pirates survived a scare to beat Richards Bay 3-1 in the Nedbank Cup last 32 at King Zwelithini Stadium in Durban on Sunday to progress to the last 16.
It was not an impressive performance from the Buccaneers as they were pushed by a determined Bay, but in the end experience won the last-32 clash for them.
They looked disjointed after taking a quick 2-0 lead. The Natal Rich Boyz will feel unfortunate as they had enough chances but could not convert them and were probably the better side in the second half.
Patrick Maswanganyi scored the lightning first-half brace in the 22nd and 26th minutes and Tshegofatso Mabasa added a late goal three minutes into added time to help the defending champions progress.
Yanele Mbuthuma struck in the 47th minute for the home side to make for a nervy second half, with the score at 2-1, for Pirates.
The Buccaneers were without captain and centreback Nkosinathi Sibisi, who was serving a one-match suspension, while Melusi Buthelezi started in goal ahead of Sipho Chaine, who was one match away from suspension.
The Natal Rich Boyz missed Justice Figareiro and Moses Mthembu.
Coach Jose Riveiro's Bucs made a lively start and the pressure paid off as Maswanganyi broke the deadlock with a shot on the edge of the box that looped away from goalkeeper Ian Otieno after he combined with Relebohile Mofokeng.
Maswanganyi completed his brace four minutes later as he combined with Mofokeng again to make it 2-0.
After scoring those two goals, Pirates were guilty of taking their foot off the pedal and allowing Bay to come at them, giving the KwaZulu-Natal chances to score.
Thato Mohlame was unfortunate not to pull a goal back with a strike that ricocheted off the post. That encouraged the home side as moments later Somila Ntsundwana had a chance, but his volley went outside as Bay finished the half the stronger side.
Bay pulled one back through Mbuthuma, who slotted home a rebound after Buthelezi parried back to play immediately after the interval.
The Buccaneers struggled to get going in the second half and the home side kept asking questions and creating chances but missed them.
Pirates were too casual in the second half as the hosts were in control. Bay were made to rue their chances missed as Mabasa sealed the victory deep in injury time when he slotted home after a through-ball by Kabelo Dlamini.
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