The challenge before them seemed insurmountable.
Not only was there a solitary qualifying spot for next year's Olympic Games up for grabs, but history was also there for the taking, for no Singaporean before them had managed to win an International Sailing Federation (Isaf) World Cup leg.
Neither of these obstacles in Qingdao last month proved impossible though for Nacra 17 sailors Justin Liu and Denise Lim, as they recorded 10 wins out of the 13 races to complete a dominant victory and earn Singapore an Olympic berth.
The Nacra 17 catamaran will be making its Games debut, with a mixed-gender crew.
Nominations for the Singapore Sailing Federation's internal selection trials close on Nov 1. Liu and Lim, helm and crew respectively, will be guaranteed their ticket to Brazil if no other teams step forward.
In the meantime, their historic feat in China earned them another accolade yesterday, when they picked up The Straits Times' Star of the Month award for September.
The prize is an extension of ST's Athlete of the Year accolade, launched in 2008. Both are backed by F&N's 100Plus.
This is the second time that Liu, a two-time Asian Games gold medallist, has received the prize. He and then partner Sherman Cheng were honoured in 2010 for their triumph at the 420 World Championships.
Said Liu, a third-year National University of Singapore business and economics student: "There was a lot of pressure which we placed on ourselves to do well but yet there's still disbelief that we pulled it off."
While the couple, both 24, have been dating for nine years, their partnership on the waters is relatively new as they rarely competed together in mixed-gender races.
But an 18th-placed finish on their Nacra 17 debut at Germany's Kieler Woche regatta in June last year lit a spark and gave them the confidence to press forward.
Said Lim, a nurse at Changi General Hospital's accident and emergency department: "We were totally new to the boat and quite apprehensive initially. The Nacra 17 is faster than anything either of us had ever sailed and we had practically no training with it.
"But that result was a huge boost and made us believe it's possible to dream of sailing at the Olympics."
The path was anything but straightforward though.
A string of poor results - they failed to finish inside the top 35 of their next three regattas - led to their partial funding from the Singapore Sailing Federation being cut. They had to spend $80,000 of their savings to continue their campaign.
Things looked even more bleak when they finished 50th at the World Championships in Denmark in July, well out of contention for the coveted Olympic spot.
But they never lost faith in themselves and a month later completed a remarkable turnaround in China.
Marc Lim, sports editor of The Straits Times, said: "Despite each obstacle that stood in their way, Justin and Denise refused to quit and found a way to overcome these challenges.
"Government funding for sports here is limited but these two didn't let that stop them. They showed great tenacity and perseverance in pursuing their dreams."
A measure of how far they have come can be seen in their world ranking.
In July 2014, they were 108th. Now, they are 30th in the latest Isaf standings, making them the highest-placed Asian team.
There is no resting on their laurels though, said Liu.
"We're already planning our training schedule leading up to Rio to give us the best chance of peaking there and, hopefully, we'll be able to do Singapore proud."
PRESENTED BY 100 PLUS