Now, what are Amakhosi's chances against a City side that could still bag three major trophies this season?
This will be Ernest Middendorp's second game against the Citizens, and having lost his first which was in the league not so long ago, this encounter promises nothing but fireworks.
Looking back at how Amakhosi fared in previous matches against City, one would say they stand a good chance of advancing to the semi-finals of the Nedbank Cup.
Also looking at their dominance in the competition over the years, they are head and shoulders above the rest.
But the pressure of winning a major trophy is resting on the shoulders of the players, and that alone could take away that away from them.
Very few players were part of the team that won the 2013 edition of the Nedbank Cup, and with this being the new squad altogether since then with the exception of the likes of Bernard Parker, Kgotso Moleko and Itumeleng Khune among others, City don't have anything to worry about.
Playing against a team that has nothing to lose could pose a threat to Chiefs, and they will have to tread carefully on the day.
City, who won the MTN8 earlier in the season, have already exceeded expectations by reaching the quarter-finals, and for them, any result would still be good enough for them although, for Benni McCarthy, there will be nothing sweeter than eliminating a team that he grew up supporting.
Chiefs were drawn against minnows in the previous rounds, and this will be a first real test of character for Amakhosi players as City will certainly be no pushovers.
Middendorp and McCarthy have both proven to be winners having already won trophies in their early careers in the PSL, but given the German mentor's experience, one can never write Chiefs even with the challenges they have faced in the early stages of the current campaign.
A win over City will mean one step into securing their first major trophy since 2015, and they can never let this opportunity slip through their fingers.
Having reached the semi-finals of the same competition last season, Chiefs at least know what it takes to get past the Last Eight and the same mental strength and attitude will be required for them to get past the Citizens.