He wanted to go 12 points clear with 12 rounds to go, but the loss of two points coupled with second-place Mamelodi Sundowns winning 2-1 at SuperSport United dashed those hopes.
READ: Chiefs held to a draw by resilient Leopards
Chiefs have 42 points, Sundowns 35, SuperSport 31 and Bidvest Wits, with three matches in hand, 30 in pursuit of a record 15 million rand ($1,040 mn/930,000 euros) first prize.
“Our ambition was to win at Leopards, but instead of collecting three points we left with only one,” bemoaned the 61-year-old, who is in his second spell as Chiefs coach.
“Having taken an early lead we allowed Leopards to come at us and paid a heavy price by conceding a foul just outside the box from which they equalised.
“I am so disappointed with the result — our hearts were set on securing maximum points from this fixture.”
Middendorp, who spent two largely unsuccessful seasons with Chiefs a decade ago, is hoping to end the longest trophy drought experienced by Chiefs since their 1970 formation.
The Soweto outfit have gone four and a half seasons without lifting a trophy after winning the 2014/2015 league title.
– ‘Chase the game’ –
Serb Samir Nurkovic, a mid-2019 signing by Chiefs from a Slovak club, raised his league goal tally to 10 with a glancing header off a corner on 11 minutes in northern town Thohoyandou.
But Leopards recovered in front of a capacity 20,000 crowd and levelled on 32 minutes when Botswana international Mogakolodi Ngele scored direct from a free-kick.
“Once again we conceded an early goal and had to chase the game. I hope holding the league leaders can be a turning point,” said Leopards coach Cavin Johnson.
He is the third coach this season of Leopards, who are among four clubs at the bottom of the table with 17 points each.
A brilliantly volleyed goal from Thapelo Morena off a cross on 65 minutes earned defending champions Sundowns victory over SuperSport in a Pretoria derby.
Themba Zwane gave the record nine-time champions a first-half lead that was cancelled by a Dean Furman penalty for SuperSport in the second half.
“SuperSport barely touched the ball during the first 85 minutes,” said Sundowns coach Pitso Mosimane. “They favoured route-one football and we comfortably dealt with that tactic.”
Wits came unstuck in windy conditions away to bottom-half Cape Town City, who triumphed 2-0 through second-half goals from Kermit Erasmus and Craig Martin.
Success was a timely boost for Dutch coach Jan Olde Riekerink, who had won only one of seven previous league matches since replacing sacked Benni McCarthy, the former South Africa star.