Noel Willcox, 48, ran up fines of £11,500 for driving a company truck to and from a depot in Harefield, North West London.
Drivers at the wheel of highly polluting vans and HGVs must pay up to £300 a day under the Low Emission Zone (LEZ) or face huge penalties.
Mr Willcox, from Berkhamsted, Hertfordshire, refused to pay and took his appeal to a tribunal, which ruled in his favour, saying Transport for London (TfL) signs for the LEZ were not ‘authorised and lawful’.
Now the businessman, from Berkhamsted, Hertfordshire, is encouraging other road users to launch similar challenges.
He told MailOnline: ‘You look at the Dart Charge or the Congestion Charge, and the signage is very clear – the white ‘C’ in the red circle.
‘It warns you on billboards on the approach, it’s written on the road surface, and then it reminds you afterwards to make sure you pay.
‘I was being literally hounded for more than a year by bailiffs through phone calls and emails, and they even came to my office.
‘It was just awful, particularly just off the back off the pandemic. It put massive pressure on me and the business.
‘The working person is being absolutely decimated by the state.’
Mr Willcox has been backed in his campaign by Nick Freeman, the motoring lawyer known as ‘Mr Loophole’.
He said: ‘While Noel’s victory is not binding on other courts, I believe the case of Elevation Access Ltd v TfL can be used by other drivers hit with penalties and fines to appeal.
‘Because this was a hearing at the first level it is not legally binding. But it is what’s known as ‘persuasive’, which means it can be used in other cases.
‘I believe the tribunal made the right ruling and TfL have got it wrong. In my view there is insufficient information on the signs. They don’t comply with the regulations.’
TfL insisted the signs were deemed lawful by the Department of Transport more than a decade ago and said it is investigating why certain evidence was not submitted.