Chiefs goalkeeper Virgil Vries was again the villain as he was in the Sundowns game, letting the ball slip through his hands from an over-hit Gift Links free-kick to gift Edmilson Dove a simple tap-in with ten minutes to go.
And Middendorp could not hide his frustration at the costly error, while bemoaning the fact that his side outplayed their opponents but were on the receiving end of a heart-breaking defeat.
"It's absolutely disappointing," the Amakhosi mentor told SuperSport TV.
"It's absolutely unnecessary to come to the end of the game with zero points. Even one point would have been something. I felt the result did not mirror the game we have seen. I can't really find the right words at this moment for this result.
The Soweto Giants had plenty of opportunities to put the game to bed in the opening half but failed to do so due to wasteful finishing and a superb performance from Cape Town City goalkeeper and eventual man-of-the-match Peter Leeuwenburgh.
"I don't know how many possibilities have been there to have a clear lead. To lose a game in this fashion is disappointing. We had opportunities, we had them very clearly on the back foot, strategically. We were definitely the much better side. But even if you have good organisation and a good strategy, in the end it has to be implemented and executed by all the players on the pitch. But conceding a goal like this is definitely not acceptable."