The 64-year-old, who arrived for his first stint with Kaizer Chiefs in July 2005, reached 400 games in the 1-0 defeat to Sekhukhune United on January 20, with the milestone going unnoticed.
However, speaking ahead of his 403rd match against Stellenbosch FC in the Nedbank Cup this weekend, Middendorp took a swipe at local coaches – naming one in particular, who has yet to come close to his numbers.
"Incredible... Incredible, because I can see sometimes when you honour players, '280, wow! 200 games played in the PSL, Jesus, my goodness, that's something,'" he teased.
"Then I'm thinking, 'If he already gets this mention with 280 games and he's already a big shot on Earth, wow.' Then I hear coaches, I don't know, big Khabo Zondo and whatever, 200-and-something – they are still only at 50% [of 400], I don't know when will they catch me in this direction. I think it's a huge compliment."
Middendorp is willing to bet that another foreign coach will not eclipse his record, at least in the next half-century.
"402 [matches], and I don't think in the next 50 years of the PSL history, there will be another foreign coach to catch me," said the German tactician.
Having infamously been in charge of Maritzburg United on four separate occasions, Middendorp argued this points to the value of his contribution and his 400-plus games on the local scene.
"Respect the decision of the chairmen and owners – they don't bring somebody in who doesn't know what he is doing, and [it's] definitely not [that if] somebody brings you back three times, you think this guy is so out of knowledge that he doesn't know what [he's doing]," he pointed out.
"402, and it will probably be more, personally, is an incredible milestone. You cannot take it away, there are no arguments. And if you start to argue or give reasons for it, you'll probably end up [thinking] that I pay the club to sign me.
"That's not the case, I'm putting some money into a retirement fund."