Robert Hazeldean had gone through a green light on a junction near Cannon Street in London during rush hour, as Gemma Brushett, 28, stepped out into the road while looking at her phone.
Despite the judge ruling the crash was 50 per cent Brushett's fault, Hazeldean failed to make a counter-claim against her, with his lack of insurance also meaning he will have to foot the legal bill as well as paying damages.
Hazeldean, who worked at a mental health charity, sounded his airhorn and swerved to try and avoid Brushett, but collided with her as she tried to step back on to a traffic island.
The pair were both knocked unconscious by the collision, with Hazeldean apparently travelling at 15mph. He was left with cuts and bruises while Brushett, who works in finance in the City and also runs yoga retreats, suffered a minor head injury.
However, the judge said "cyclists must be prepared at all times for people to behave in unexpected ways."
Judge Mauger said: "Mr Hazeldean did fall below the level to be expected of a reasonably competent cyclist in that he did proceed when the road was not completely clear."
A crowdfunding campaign has been set up to try and help Hazeldean raise the money, which could end up costing £100,000 but is likely to be less.
Detailing the costs, the online campaign states Hazeldean could be liable to pay £4,300 in compensation, payable in 14 days, £10,000 to cover the pedestrian's legal fees, payable in 21 days (this may increase when the final cost award is declared as they are seeking around £100,000 in costs - but £10,000 was the amount indicated by the judge) as well as £7,000 to cover his own legal fees.
If he had been insured the total would have been a lot less, according to Hazeldean's lawyer Emma Farrell, who said: "If Mr Hazeldean had been insured, the claimant's legal costs would have been limited to a mere £6,690.
"If he had come to us sooner, we would have advised him to enter a counterclaim given that he has been left with permanent scarring, both physically and mentally.
"He would then have had protection under the law against a large costs order."
A spokesperson for her firm, Levi Solicitors, added: "We believe that the law in this area urgently needs reforming."
Following the crash and court case, Hazeldean moved to France for a "new life", getting work as a garden designer, and says the four-year ordeal has taken a toll on his mental health and left his future uncertain.
Writing on the crowdfunding campaign page, Hazeldean said: "This verdict brings to a close four years that have taken a great toll on my mental health. I am of course deeply disappointed with the outcome, reeling from the impact it will have on my life, and concerned by the precedent that it might set for other cyclists.
"I would urge other cyclists to take out insurance through British Cycling to help protect them from experiencing what I’ve gone through.
"The case has cast a shadow over our new life in France and left our future uncertain. Covering the costs and the compensation is going to exceed £20,000 and will leave me bankrupt. I can only hope that the focus on this case highlights the vulnerability of cyclists, both physically and against the courts, and that it might help reform a legal system that appears to leave certain road users disproportionately exposed."
Brittany Maher-Kirk, who set up the Go Fund Me page for her friend, told Cycling Weekly: "As a friend and a fellow cyclist, I couldn’t stand by and do nothing. Putting the mental and physical damage to Robert aside, this is about so much more than one man and his bike - it sets a worrying precedent for cyclists across the country.
"What happened to my friend could have happened to any one of us who gets on a bike every day, I can’t say thank you enough to everyone who is sharing and donating."
The campaign has already raised £3,000 after being live for less than a day, with the fundraising goal set at £21,000. You can find out more information here.
Thank you for reading 20 articles this month* Join now for unlimited access
Enjoy your first month for just £1 / $1 / €1
*Read 5 free articles per month without a subscription
Join now for unlimited access
Try first month for just £1 / $1 / €1