With both sides eyeing a spot in the quarter-finals, the encounter is bound to produce fireworks at the iconic Cape Town Stadium.
However, Goal looks at how the Citizens boss, Benni McCarthy, can bring the high-flying Buccaneers down to earth.
Pirates have rested enough for the clash since their win over Soweto rivals, Kaizer Chiefs in the Derby a week ago compared to City, who just came back from Mozambique in the Caf Confederation Cup.
A look at how coach Milutin Sredojevic managed to beat top sides such as their rivals, Mamelodi Sundowns and Amakhosi, could signal to McCarthy that he must be wary of Bucs.
Following Pirates' 1-0 win at the FNB Stadium in the league back in September, the hosts will be chasing a win to avenge the loss suffered in the Premier Soccer League last year.
Thabo Qalinge netted the only goal of the game, but McCarthy will face the likes of Thembinkosi Lorch, Musa Nyatama and Luvuyo Memela, who are ready to cause all sorts of problems for any defence.
Despite losing 3-1 to Sundowns at the Orlando Stadium in the first round, Sredojevic went to Tshwane and stunned the PSL log leaders with the same scoreline to avenge their loss.
In front of their home crowds, a word of advice to McCarthy is that he must create goalscoring chances and find a goal as early as possible.
Looking at their game against Amakhosi in the Soweto Derby and against Chippa United prior to the Derby, the Ghosts were asleep in the first half of these two games.
Steve Komphela’s men dominated the match in the opening half, but were left to rue their failure to turn that dominance into goals in the second period.
McCarthy must punish Pirates in the opening half and avoid taking time to settle down in the second half. Pirates usually score early in the second half to take control of the game.
Micho is motivated after beating the two big guns in the Brazilians and Chiefs with the same margins, and heading to the Western Cape means his men are favourites.
So, what must McCarthy do to stop the new look and refreshed Bucs?
Players such as Teko Modise and Roland Putsche should work in hand-in-hand in order to stop the Musa Nyatama, Marshall Munetsi, Xola Mlambo partnership in the middle of the park.
Nyatama is a great passer of the ball and his eye for a defence-splitting pass in search of Justin Shonga, who is always ready to make a run behind opposition defence, could be troublesome for City if they fail to close him down.
The former Sundowns man is not the only man who’s providing mobility and danger in the team, but the likes of Memela and Lorch are getting great supply from Nyatama – closing him down means half of the job will be done.
Apart from that, Benni should partner Tshepo Gumede and Kwanda Mngonyama in central defence.
Mngonyama will provide height for aerial balls whilst Gumede is perfect for reading the game and guard against the through balls launched by Nyatama and company.
Ayanda Patosi, Craig Martin and Thabo Nodada as well as Sibusiso Masina must all bring their A-game to stun and keep the Pirates defence on their toes.
Pirates have good goalkeepers in Siyabonga Mpontshane and Jackson Mabokgwane, but they can be easily beaten, especially when their defence is put under pressure.
The two coaches are clever and plan well and fans can expect a tactically planned contest by both coaches.
For the Citizens to win it, the use of counter-attacking football will be detrimental, especially if Pirates scores first because that will mean City must go and chase the game, thus opening up at the back.
McCarthy is a winner and has not employed transitional tactics for now, but he must score goals as early as possible to ensure they do not become the Buccaneers’ eighth victim (in all competitions) in 2018.
Should McCarthy’s men fail to score in the opening half, they will be inviting trouble because Pirates currently look very dangerous in the second half of their games this season.