Amakhosi face a Cape Town City team that hasn't lost a match in their previous six outings across all competitions.
But history is firmly on Amakhosi's side as they have won all three of their last three matches against Cape Town City.
What makes the encounter even more interesting is the fact that Chiefs managed to beat City even when they were not at their best.
Earlier this season, Chiefs hammered Cape Town City 4-1, and at the time, they were still trying to find their feet under former coach Giovanni Solinas.
Now, there is a new sense of belief among the players and Middendorp, while his team has lost three of the last six matches in all competitions, appears to be heading in the right direction with the current squad.
Chiefs players look more focused than ever in the league, and the fact that they are no longer giving away goals cheaply means Middendorp is doing something right.
Benni's charges know what to expect from Chiefs, but they should be wary of a team that is still licking its wound after all that has happened this season.
There are also several Chiefs players who have been underperforming in recent weeks, including Khama Billiat, and that alone could be a deciding factor as everyone in Middendorp's team wants to shine and prove that they deserve to be wearing the famous gold and black shirt.
Hendrick Ekstein is one player that City should keep a close eye on. The midfielder has undoubtedly regained his confidence, and he's showing glimpses of what Amakhosi fans saw in him a few years ago whilst representing the team in the MultiChoice Diski Challenge.
Even without their regular stars such as Itumeleng Khune and Erick Mathoho, Chiefs are still dangerous. City may consider themselves unlucky that they have only beaten them once in the last two-and-a-half years.
While it may seem impossible for Chiefs to mount a serious challenge to the league title, the fact that they are still a few points behind log leaders Bidvest Wits could be motivation enough for the players going into this game.
They also crashed out of the Caf Confederation Cup which will give them enough time to prepare for league matches and juggle them with Nedbank Cup matches.
Middendorp's team may look blunt upfront with Billiat off-form, but they are doing a good job defensively, especially in the league matches which is why City should be concerned as they enter their territory on Wednesday night.