The Natal Rich Boys were unbeaten in five Betway Premiership games before losing 4-1 to Mamelodi Sundowns in their last league game.
But they come into this tie on the back of a solid 4-1 Carling Knockout first round victory over Chippa United before the international break - and in tenth place on the standings with 11 points from nine games.
Orbit, meanwhile, are down in 13th place with seven points. They lost their Carling Knockout clash 1-0 to TS Galaxy after a 3-0 defeat to Golden Arrows, but did manage to pick up four points in September with a 1-1 draw with Marumo Gallants and 1-0 win over Polokwane City.
They had turned to experience in their first season in the South African top-flight with a number of quality signings, namely Monnapule Saleng, Thuso Moleleki, and Yanga Madiba (on loan from Orlando Pirates), Thato Mohlamme (Richards Bay), Lucky Malatsi (Lerumo Lions), and Yamkela Gamede (Hungry Lions FC).
But with performances still underwhelming, the club have since added former Mamelodi Sundowns and Kaizer Chiefs defender Ramahlwe Mphahlele, Lebohang Lesako, formely of Kaizer Chiefs and Casric Stars, and midfielder Papama Tyongwana, who has previously played for Chippa United.
Ahead of the game, Bay coach Ronnie Gabriel said he feels his team are improving after a poor start to their season.
"It was not the fastest of starts this season,” Gabriel said in the Herald.
"In our first three league games, we didn't get any positive result, but we continued to believe in the blueprint of the club, which is giving youngsters a chance.
"It was going to take time for them to acclimatise to the level of the league. We are playing with a lot of youngsters, but after the first three games, they started to come out, and they are showing that they are capable of competing at this level.
"We went on a five-game unbeaten run at some point. It has everything to do with the belief we've shown, trusting the processes, and it is slowly paying dividends."
Following a difficult start to life in the Betway Premiership, newly promoted outfit Orbit College have strengthened their squad with the signings of experienced campaigners Ramahlwe Mphahlele, Lebohang Lesako, and Papama Tyongwana.
Richards Bay and cup holders Magesi both progressed to the quarter-finals of the 2025/26 Carling Knockout with victories in the last 16 on Sunday.
The Carling Knockout delivered eventful encounters on Saturday as TS Galaxy and Golden Arrows secured victories to march into the quarterfinals.
TS Galaxy coach Adnan Beganovic says his side must quickly bounce back from their midweek Betway Premiership loss to Orlando Pirates.
