The Soweto giants are heading into this encounter undefeated in their last six matches in the Premier Soccer League (PSL).
However, they are winless in their last two games having drawn 1-1 with AmaZulu FC away in their most recent game two weeks ago.
The Telkom Knockout presents Pirates with an opportunity to end their four-year trophy drought.
The Buccaneers, who have won the Telkom Knockout once (in 2011), were eliminated in the quarter-finals by Polokwane City, who won 4-2 on penalties following a 2-2 draw at home last season.
|Game||Orlando Pirates v Chippa United|
|Date||Saturday, October 20|
|Time||8:15 pm SA Time|
TV Channel, Live Score & How To Watch
|Live Match Centre||TV Channel|
Squads & Team News
Pirates head coach Milutin 'Micho' Sredojevic will look to Zambia international Augustine Mulenga, who has established himself as a key attacker for the team.
The skilful forward was on the scoresheet against AmaZulu taking his tally to three goals in all competitions for this season.
Bucs have been boosted by the return of Brilliant Khuzwayo and Vincent Pule, who were both nursing injuries.
Predicted Pirates line-up: Khuzwayo, Matlaba, Maela, Jele, Marcelo, Mlambo, Motshwari, Mako, Lorch, Pule, Mulenga.
Meanwhile, Chippa are heading into the Cup clash having lost 2-1 to Highlands Park away in a PSL encounter two weeks ago.
The defeat ended the Chilli Boys' three-match unbeaten run in the league having recorded two wins and one draw.
They were defeated in the 2017 Telkom Knockout quarter-finals by Kaizer Chiefs, who emerged 1-0 winners away.
The Eastern Cape-based outfit has never won a major trophy and Eric Tinkler's side will be hoping to stun Pirates, and go on to win the trophy.
Tinker, who is a former Pirates head coach, won this tournament with Cape Town City two years ago as he masterminded a win over SuperSport in the final.
Tercious Malepe has been in good form for the Chilli Boys since joining the club from Pirates on a season-long loan deal.
The versatile player, has grabbed two assists in Chippa's last two games, will look to play an important in helping his side overcome Bucs.
Predicted Chippa line-up: Akpeyi, Tlolane, Nsabiyumva, Macheke, Nthethe, Komane, Malepe, Mayambela, Lentjies, Klate, Mbenyane.
This will be the first cup meeting between Pirates and Chippa.
However, the two teams have clashed in 11 PSL matches since 2012/13, with Bucs securing seven wins compared to Chippa's three wins.
Pirates secured a narrow 1-0 win over Chippa at home in a league game two months ago.