Alan Curtis, 57, from Bushey in Hertfordshire, suffered a "severe head injury" in the crash on The Drive, Rickmansworth, in 2009.
He sued Hertfordshire County Council for failing to fix the pothole, which he said was a "real source of danger".
The council said it was "disappointed" the High Court had ruled in Mr Curtis's favour.
Mr Curtis, a charity fundraising director, was cycling with two friends when a "defect" in the road surface caused him to lose control, fall from his bike and hit his head.
Kevin O'Sullivan, from Levenes solicitors, said Mr Curtis had experienced "pain, suffering and loss of amenity".
"Potholes tend to cause [cyclists] more serious injuries than accidents involving motor vehicles and this is a classic example," he said.
The claim stated the pothole could be seen on a Google Street View image from October 2008, but the council failed to note it and order its repair during a scheduled inspection the following March.
Mr Curtis fractured his skull and damaged his brainstem, which led to "significant deafness", the claim stated.
His left arm was also broken.
Mr Chambers, who had been wearing a safety helmet, was given emergency treatment at Watford General Hospital.
A report from neuropsychologist Dr Yvonne McCulloch said "cognitive impairments" caused by the brain injury had hampered Mr Curtis in the workplace since the accident.
He has since switched to a similar, but less stressful, job which has meant a loss of earnings.
A cyclist who was thrown from his bike when it hit a pothole has been awarded nearly £70,000 in damages.