During the 2008 Beijing Olympics, Singapore sent its largest contingent at that time, since it first participated, and was considered the best prepared to win a medal.

[12] Li Jiawei, together with Feng Tianwei and Wang Yuegu, beat the South Korea Women's Table Tennis team, composed of Dang Ye-Seo, Kim Kyung-Ah and Park Mi-Young 3–2 in the semi-finals, assuring Singapore of at least a silver medal and ending Singapore's 48-year Olympic medal drought.

[14] In the table tennis women's team bronze medal match, Li, together with Feng and Wang, beat the South Korea team composing Dang Ye-Seo, Kim Kyung-Ah and Seok Ha-Jung 3–0, winning another bronze medal.

[18][19][20][21] During the 2020 Summer Olympics held in Tokyo, Japan, Singapore sent 23 athletes to the Games but did not manage to win any medals.

[22] In the 2024 Summer Olympics in Paris, kitefoiler Maximilian Maeder won a bronze medal in the Men’s Kite category at the age of only 17, coming behind second place Toni Vodišek from Slovenia and first place Valentin Bontus from Austria.