Scott Taylor, who was 19 when the accident occurred, has asked the High Court in Durban to set a trial date to claim millions in damages from the city.
Taylor, now living in England, was paralysed from the waist down after hitting a tree after apparently riding into a pothole.
His father, Alfred Taylor, a former deputy chief constable in Durban, is also suing for hospital bills and the cost of alterations to his home needed to accommodate his son's disability.
They claim in affidavits, filed 20 years ago, that the then Durban city council failed to maintain and repair the road. At the time, the council denied it was negligent and blamed Scott, claiming he had contributed to the accident. It did not elaborate.
The municipality now has until September to oppose the latest application.
Durban attorney, Anne Martens, representing the Taylors, said 20 years ago the courts were hesitant to hold municipalities responsible. She said changes in the interpretation of the law made conditions for going to trial ''far more favourable".
In 2008, Pietermaritzburg advocate and cyclist Allistair McIntosh was awarded R15-million when he sued the provincial department of transport after he hit a pothole in 2004.
This week the Taylors, who initially filed separate claims for damages, applied to the court to consolidate their cases into a single court action.
Martens said the Taylors' initial combined claim of more than R3-million would have to be revaluated according to the current economic climate.
In court papers Scott said the accident happened when he hit ''potholes or a rut or a crack'' in a road near the city's Botanic Gardens. He lost control and crashed into a tree. He claims the municipality was negligent in failing to maintain and repair the road and claimed it ''failed to alert the public or warn of the danger".
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