The 21-year-old battled back from a serious injury sustained in a horrific pre-Olympics training accident that all but wrecked her chances at the summer's London Games - only to find her sport replaced by the International Sailing Federation (ISAF) in favour of kiteboarding at the next Games, in Rio de Janeiro, in 2016. Her chance to ever set the record straight, it seemed, had gone.
Again refusing to accept defeat, Chan joined a spirited lobbying effort by the windsurfing community that ended in success last week when it was reinstated by the ISAF over its rival sport.
Reflecting on a whirlwind few months, a happy - and relieved - Chan recounted her struggles. To prepare for London, the first-year English literature student suspended studies at the University of Hong Kong to become a full-time professional windsurfer, and headed overseas to gain top-level international experience ahead of her medal bid.
Her sacrifice appeared to have paid off when she ousted more senior compatriot Vicky Chan Wai-kei to grab the only women's place in the Hong Kong windsurfing team.
The 2009 Youth Sailing ISAF world champion, Chan went to England two months early to acclimatise to local conditions. Tragically, only weeks before the opening ceremony, her campaign came to a shattering halt when she collided with a 49ft yacht in a freak training accident.
"The boat was on my blind side and when I saw it, it was too late to avoid a crash ... After the impact I could hardly breathe," Chan said. She was diagnosed with five broken ribs and a ruptured spleen.
"I did worry that I may not be able to race after all my hard work," she said. "But when I arrived at the hospital, the pain forced me to put the Olympics aside. I started to wonder if I would die there."
Doctors ordered immediate surgery. "I had to do it, to have a chance of a speedy recovery. I thought I could still have a slim chance of competing in the Games."
And the sailor with the iron will succeeded, wearing a modified taekwondo body protector to make a comeback on the water barely a month after the accident.
It was still touch and go for the Games but, after rigorous medical checks by Hong Kong team doctors, she was pronounced fit; something of a miraculous recovery.
On the first race day, July 31, Chan's comeback was complete when she sailed up to the starting line. "I could hardly believe it wasn't a dream, the moment I put my board on the water," she said. "I was still there, after going through so many challenges! I was so happy."
She finished a creditable 12th overall in London, the best among Asian women, but was still left to wonder what might have been.
Then came the bombshell that windsurfing was to be dropped from the Olympic roster and the realisation she would never have another chance.
Determined Chan set about lobbying to overturn the decision. "I got contacts from my coach Rene [Appel]. I had to do something. I wrote e-mails to express my point of view, and explain how much I wanted to compete at the next Games."
The protest paid off when, at last week's ISAF annual conference in Ireland, windsurfing regained its prized Olympic status.
To a delighted Chan, nothing could be better than seeing the sport she loves back in the world's greatest multi-sport event.
Having defended her Women's RSX title at the Hong Kong Open last Sunday, she has decided to put her studies back on hold for another shot at glory in Rio.
"Windsurfing being back in the Games means I have to give my full commitment to the sport for four more years," said Chan.
"And I aim to win a medal in Brazil in 2016."