On Sunday, sailors Bernie Chin and Samantha Yom won Singapore's first gold medals at the Youth Olympic Games (YOG) in Nanjing - both of them came in first in the men's and women's Byte CII events. Here is a look at the Republic's other medallists at the Summer Olympics, Paralympics and YOG.
Tan Howe Liang (silver, 1960)
The weightlifter, now 81, remains a hero to Singaporeans for winning the country's first Olympic medal - A silver at the Rome Olympics. Tan did not enjoy generous funding and he had to battle pain in his legs when he hoisted a total of 380kg in the clean and jerk to come in second.
He competed in the lightweight category but Tan's achievements are anything but that.
Feng Tianwei, Li Jiawei and Wang Yuegu (silver, 2008; bronze, 2012)
(From right) Feng Tianwei, Li Jiawei and Wang Yuegu
This trio of China-born paddlers ended Singapore's 48-year-old drought for a second Olympic medal when they chopped and smashed their way to a women's team silver at the Beijing Olympics.
Four years later, they earned a bronze in London. Shortly after, Li and Wang retired from the sport but Feng has stepped up to lead a new generation of players gunning for more Olympic glory in Rio de Janeiro in 2016.
Feng Tianwei (bronze, 2012)
Drawn against then-world number one Ding Ning from China in the semi-finals in London, sixth-seed Feng put up a strong fight but ended up losing 2-4 in the semi-finals.
But her technique and relentless attacks proved too much for Japan's Kasumi Ishikawa, ranked fourth in the world at the time, in the bronze medal playoff to bag Singapore's second individual medal at the Olympics.
Youth Olympic Games
Daryl Tan (bronze, 2010)
Daryl Tan has the distinction of being the first Singaporean medallist at the inaugural YOG hosted on home soil when he made it to the semi-finals of the men's Under-55kg taekwondo competition.
Although he did not make it to the final, he still won a medal as both losing semi-finalists were awarded joint bronzes.
Shafinas Abdul Rahman (bronze, 2010)
Shafinas gave the home crowd more to cheer about a day after Daryl's feat when she also bagged a bronze medal after making it to the semi-finals of the women's Under-55kg taekwondo event.
What made the ex-netballer's achievement more remarkable was that she competed during Ramadan.
Rainer Ng (silver, 2010)
Rainer's silver in the men's 50m backstroke event was the third YOG medal for Singapore at the 2010 Games.
The swimmer was just 0.09 second behind Trinidad and Tobago's Christian Homer - and earned him the nickname "Silver Surfer" after the Marvel Comics character.
Isabelle Li (silver, 2010)
Isabelle came closest to winning the Republic's first gold medal at the YOG but she lost out 0-4 to China's Gu Yuting in the final.
But the plucky Singapore-born paddler earned loud cheers from the home crowd. She had since progressed to the senior national team and recently won a team gold medal at the Glasgow Commonwealth Games.
Abdul Dayyan (bronze, 2010)
Pairing up with Turkey's Elif Begunhan Unsal, Abdul and his partner were on the verge of losing their bronze medal playoff to Spain's Miriam Alarcon and Bangladeshi's Mohamed Emdad Haque Milon.
Tied at 5-5, the latter pairing scored 19 out of 20 points in the shootout but Elif and Abdul both hit the bull's eye to defeat their opponents by a point and win the medal in thrilling fashion.
Audrey Yong (bronze, 2010)
Having won a bronze in the Techno 293 sailing event at the Asian Youth Games a year earlier, Audrey repeated the feat at the 2010 YOG to prove that it was no fluke.
She finished behind Thailand's Siripon Kaewduang-ngam and Italy's Veronica Fanciulli.
Singapore football team (bronze medal in men's football, 2010)
Playing a brand of expansive attacking football, this bunch of boys entertained crowds at Jalan Besar with spectacular goals and cheeky celebrations.
After a heartbreaking 0-2 loss to Haiti that denied the Singaporean boys a chance to go for a rare gold in international football, the national football team dispatched Montenegro 4-1 to win bronze in front of a passionate 6,000-strong crowd. Sadly, none of the players, now 19, have featured for the senior Lions.
Martina Lindsay Veloso (silver, 2014)
Veloso has emerged as a genuine shooting star in 2014. The 14-year-old followed her stunning gold medal win at the International Shooting Sport Federation (ISSF) World Cup in Munich in June with a silver at the Nanjing YOG in women's 10m air rifle,.
Looking likely to get only the bronze medal at the last shot, Martina managed to overcome a 0.9 lead over Germany's Julia Budde to finish second and earn Singapore's first medal at the 2014 YOG.
Teh Xiu Yi (silver, 2014)
Having lost in the individual 10m air pistol event final after she was unable to concentrate due to the boisterous crowd and loud music played over the speakers, Xiu Yi learnt to shut out the distraction and went on to win silver in the mixed team's 10m air pistol event.
Teaming up with Egypt's Ahmed Mohamed, the duo lost out to Bulgaria's Lidia Nencheva and Vladimir Svechnikov of Uzbekistan 5-10 in the final.
Laurentia Tan (bronze, 2008; silver/bronze, 2012)
Tan won Singapore's first medal at the Paralympics when she earned bronze in the individual championship test (Grade 1a) at Hong Kong's Shatin Equestrian Complex in 2008. The United Kingdom-based equestrienne, who is deaf and suffers from cerebral palsy, followed up that triumph with another bronze in the individual freestyle test.
Four years later, in London, Tan followed up with a silver in the individual freestyle test and a bronze in the Grade IA individual championship dressage test.
She remains the only Asian equestrian medallist so far in the history of the Paralympics.
Yip Pin Xiu (gold/silver, 2008)
Yip won Singapore's first gold medal at an Olympic-level event when she came in first in the women's 50m backstroke final at the 2008 Paralympics in Beijing.
Born with muscular dystrophy, a disorder which essentially sees her body progressively degenerate, the gutsy Yip did not let her condition bother her as she won another medal, a silver in the 50m freestyle as well.