The Manchester United boss featured in the comedian's video as part of a new YouTube series, called 'Training Days'.
The Special One attacked the task with a no-nonsense approach, but his patience was immediately tested.
After Whitehall stalled the car, Mourinho joked: "I prefer a player without a brain than teach you how to drive."
As the 29-year-old began to drive the car, the Portuguese boss provided some stern words of encouragement.
He shouted: "Don't kill anyone, that's good!
"Forget the brake! Keep going."
Whitehall picked up the basics, but Mourinho will be relieved to have escaped unscathed.
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The 55-year-old then reluctantly took the comedian for a spin in his Jaguar, equipped with a TV in the dashboard.
Mourinho likened driving to his role with the Red Devils, he said: "There are clicks in the learning process.
"One day you beat Liverpool, the next day you lose to Sevilla."
Mourinho then jokingly stormed out of the car after the comedian took a cheeky dig at his hair.
The comedian labelled him as a "silver fox" and the two stars parted ways after a successful afternoon.
Mourinho will now be preparing for United's clash against West Ham on Thursday, while Whitehall jetted off to play golf with Gareth Bale.
Whitehall then made the Welsh superstar hilariously prank people in a waxwork museum
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