The Sea Robbers advanced to the final of the CAF Confederations Cup following their 1-0 loss to A Ahli Tripoli at Orlando Stadium on Sunday.
In 1995 EzikaMagebhula became the first South African club to win silverware in Africa by winning the CAF Champions Cup over Asec Mimosas before they went on to clinch the CAF Super Cup.
In 2013 De Sa guided the Soweto giants to the final of the Champions League but ultimately came unstuck against Egyptian giants Al Ahly.
Two years later Eric Tinkler steered Bucs to the Confederations Cup final where they lost to Etoile du Sahel.
"I think they've got a good chance this time, we were inexperienced last time, but this time around they should know what they are there for," De Sa tells KickOff.
"RS Berkane they are a tough team, but I think they (Pirates) should do it for sure, my money is on them, they going to win it.
"The main thing is to not concede at home, that's number 1, don't concede at home, that's all.
"We didn't make any mistake to be honest (Against Ahly in 2013 in the CCL), they were just better than us, they were more experienced than us.
"We had a lot of injuries Andile Jali didn't play and Happy Jele didn't play because they were both suspended, we had Benni McCarthy injured, we had a lot of problems but still we put up a good fight."
Vilakazi says co- coaches Mandla Ncikazi and Fadlu Davids did well to put Pirates in the final.
"They did well to take the team to Confed Final," Vilakazi says,
"It's something some of us saw coming because Pirates do have players,
"They just need somebody who will put players in their correct positions and get the best out of them.
"That's all that they need right now.
"Ya so well done to the team for making it into the final.
"I think they will definitely win the final come rain or shine."