In 1965, two poor Singaporean children, Chew Kiat Kun (Shawn Lee) and his younger sister Seow Fang (Megan Zheng) live with their mother (Xiang Yun) who is late in her third pregnancy and their father (Huang Wenyong) who is in debt to a local rice merchant. The children make the best of what little they have, while their father works long hours doing odd jobs.

The family's problems are compounded when Kiat Kun accidentally loses Seow Fang's only pair of shoes after taking them to be repaired. The children conduct a frantic search but find nothing; a karung guni man had claimed the shoes as unwanted rubbish. The Chew siblings are frustrated and rendered helpless by the situation until their father inspires Kiat Kun to share his shoes with his sister, trading off between classes so they can both attend school. Unfortunately, this plan brings additional problems: Seow Fang is chastised for wearing oversized shoes to school, while Kiat Kun is repeatedly late as he must wait for his sister to exchange shoes with him.

At school, a wealthy schoolmate of Kiat Kun's named Tan Beng Soon (Joshua Ang) runs an amateur football team with his friends. Kiat Kun and his friends strike a bargain with Beng Soon to play on the team using the other boys' football shoes, in exchange for helping them cheat on their homework. However, the boys quarrel, causing an angry Beng Soon to renege on the deal and remove Kiat Kun and his friends from the team.

Without their assistance, Beng Soon and his friends are punished for producing substandard homework. Although the boys try to resolve their differences, they eventually give up on reaching an agreement, and Beng Soon's grades continue to fall, so his parents decide to send him away to study in England. Kiat Kun, on the other hand, is often late, so the headmaster decides to expel him, but he was accepted again thanks to another teacher's defense, acknowledging his dire family background.

Meanwhile, Seow Fang sees her classmate wearing her lost shoes to school. She and Kiat Kun follow the girl home, but after realising her father is blind and that her family was in a more dire situation than theirs, they decide not to reclaim the shoes. However, a few days later, Seow Fang notices that her classmate is wearing a new pair; upon confronting her, she discovers that the girl has discarded the old pair at the kampung rubbish dump. The Chew siblings frantically search the rubbish dump for her shoes, but only discover them as they are destroyed during a trade unionist riot against a policeman (Wakin Chau).

The climax of the film, in which Kiat Kun is pushed to the limit but trips and finishes first — a parallel to Singapore's political history.

Kiat Kun is dejected until he learns that the third prize in the 1965 National Primary School Cross Country Competition is a pair of shoes. Because he was sick on the day his school selected representatives for the race, he pleads with his P.E. teacher to let him enter. The teacher, initially reluctant, relents when Kiat Kun rushes to get his cough medicine, demonstrating his running ability. As the competition begins, Kiat Kun notices that Beng Soon is also participating.

Once the starting gun fires, Kiat Kun pushes himself to the limit and eventually establishes himself among the lead runners. Kiat Kun appears assured of third place, but unexpectedly trips over a stone and thus finishes first. Beng Soon ends the race in third place. While Kiat Kun is running, Mrs Chew goes into labour, forcing Seow Fang to run across a long path littered with broken glass to find a midwife. Finally, Mrs Chew gives birth to a baby boy and Beng Soon gives Kiat Kun and Seow Fang new pairs of shoes before departing for London. 1

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