Manchester City chairman admits Pep Guardiola nearly resigned 100 times during his tenure
Guardiola left his role after securing six Premier League titles and the Champions League during his sparkling decade at the Etihad Stadium.
Although Guardiola achieved exceptional success at City, Khaldoon revealed that the passionate Spaniard frequently considered stepping away during difficult periods of his tenure.
"Over the past decade, we have experienced many highs and some lows. During the tough times, he must have resigned 100 times across those ten years, just for the record," he stated to City's media outlets on Thursday.
"You are all familiar with the tale of the boy who cried wolf. With Pep, when he announces he is leaving, it does not mean he is actually resigning. You should not take it too literally; you need to handle him carefully.
"Whenever he expresses a desire to step down or feels the moment has come, I would always persuade him to stay, until the point when I realised it was genuinely the right time. We reached that stage. I understood it, and that is why I did not oppose it."
Guardiola claimed 20 trophies during his time at City, among them the FA Cup and League Cup in his final campaign.
However, the 55 year old resigned after acknowledging that he no longer possessed the vigour necessary to push City ahead.
'Far from our peak'
City have now gone two seasons without claiming the Premier League title and ended this campaign seven points adrift of champions Arsenal, leading to suggestions that they are no longer the dominant side they used to be.
In response to the criticism, Khaldoon remarked: "We are far from our peak. We are accustomed to winning; it is part of our DNA. This club is structured and constructed to triumph.
"With the reinforcements we will bring in this summer, I am extremely confident. I believe we will return very strong next season."
Former Chelsea boss Enzo Maresca is anticipated to be confirmed as Guardiola's successor in the near future.
Maresca secured the UEFA Conference League and Club World Cup with Chelsea, and he served as Guardiola's assistant during the 2022-23 season at City.
When questioned about City's succession strategy for the manager role, Khaldoon said: "At this stage, I can only say that we have undertaken a careful and organised procedure. The team is confident, and I am confident, that we will secure the appropriate manager for this club.
"Please be patient with us. We will make an announcement very shortly, and you will be entirely satisfied that we have chosen and appointed the best possible manager."