Currently seventh on the log with 19 points from 13 games, City will be up against a Pirates squad eager to secure a win that could put them at the summit of the table.
South African football legend and former PSL coach Mlungisi Ngubane believes Durban City may have already made a critical misstep ahead of the clash.
"Taking matches against the Big Three to Moses Mabhida Stadium has always worked against KwaZulu-Natal teams," Ngubane told KickOff.com.
"It's a venue that favours Pirates. They should have considered Chatsworth Stadium to play in an unfamiliar environment."
Ngubane also highlighted the challenge Pirates' substitutes pose.
"Chippa United tried to contain them and still couldn't manage the impact of the substitutes. Pirates are hard to plan against because every player can score," he said.
While acknowledging City's determination, Ngubane warned that their best might not be enough.
"They will give their all, but Pirates' quality is difficult to overcome."
He concluded by praising the consistency of the Buccaneers and AmaZulu FC this season
"Pirates and AmaZulu are showing the most consistency. By Monday, Pirates could very well be at the top of the table."