The Buccaneers, guided by head coach Abdeslam Ouaddou, are under early pressure after consecutive defeats in their opening fixtures.
A 1-0 loss to Sekhukhune United was followed by a 2-1 setback at Marumo Gallants, leaving the Soweto giants still searching for their first points of the campaign.
Their cup form, however, has been more encouraging. Pirates advanced to the MTN8 semi-finals after a 2-0 win over Polokwane City and earned a 1-1 draw with Mamelodi Sundowns in the first leg of the last four.
Stellenbosch arrive in Johannesburg with a similar league record, having lost 2-0 to Kaizer Chiefs before a 1-1 draw with Magesi.
Steve Barker's side, though, carry confidence from their MTN8 exploits, where they stunned Sekhukhune United 2-0 in the semi-final first leg to move within reach of a historic final.
A major concern for the visitors is the fitness of midfielder Sanele Barns. The 28-year-old, who scored twice in their quarter-final win over AmaZulu, missed the semi-final first leg with a hamstring problem and remains a doubt for the trip to Orlando.
"He's got a bit of a tight hamstring, which with all the games coming up midweek against [Orlando] Pirates and Sekhukhune next Saturday, it was just not worth the risk," said Barker.
"So, he would have played. He was in the starting team, but at training in the last 10, 15 minutes, he felt a bit of pain, so we just took more precaution than anything else."
Stellenbosch are also sweating on striker Ashley Cupido, who was forced off just seven minutes into the Sekhukhune tie with injury.
There were victories for Sekhukhune United, TS Galaxy and Polokwane City while Durban City and Golden Arrows could not be separated in Betway Premiership action that delivered plenty of goals on Tuesday.
Kaizer Chiefs continued their perfect start to the Betway Premiership season with a 1-0 victory over Richards Bay at FNB Stadium on Tuesday night.
Magesi will be looking for their first win of the new Betway Premiership season at home to Mamelodi Sundowns on Wednesday.
Bradley Cross says he welcomes competition for his place in the Kaizer Chiefs starting line-up.
