This will mark Middendorp's 18th match against the Brazilians, but how did the German mentor fare in previous meetings against the Brazilians?
He has faced Sundowns 17 times, but his record against the Tshwane giants isn't too impressive.
Middendorp may need to come up with a different plan to thwart Sundowns, who are unbeaten in the league thus far.
The 58-year-old mentor will take solace from the fact that he beat Sundowns once during his first stint, losing twice and drawing once.
But that record may not come to play this time around as Middendorp was at the helm over a decade ago.
Middendorp's first match in charge of the Glamour Boys against the Tshwane giants saw him win 1-0, while the second match was a 3-1 defeat.
His third match against Sundowns ended in a goalless draw, while he lost 2-1 in the season leading up to his sacking at the club.
Now, he gets the opportunity to rectify this mistake and make sure that Chiefs are on par with Sundowns.
So far, Middendorp has won just four games against Sundowns in all the teams that he has coached.
He drew twice and lost a whopping 11 matches - something which Chiefs should be worried about going into this encounter.
But given how well he has started since taking over from Giovanni Solinas (three wins on the trot), Chiefs may be confident of beating Sundowns to break their 24-match unbeaten run in the league which stretches back to December 2017.