| Director | Jack Neo |
|---|---|
| Budget | SGD 1.5 million |
| Box office | SGD 2.3 million |
In 1965, two poor Singaporean children, Chew Kiat Kun and his younger sister Chew Seow Fang live with their mother who is late in her third pregnancy and their father who is in debt to a local rice merchant and provision shop owner. 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 runs an amateur soccer team with his friends. Kiat Kun and his friends strike a bargain with Beng Soon to play on the team using the other boys' soccer 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 Mathematics results continue to fall, which resulted his Form Teacher named Mrs. Ang to persuade his father and mother Mr. Tan and Mrs. Tan down to school to witness Beng Soon's private caning inside the staff room before his parents scolded him for his poor performance in studies in school due to football training. His father ultimately decided to send him away to study in England. Kiat Kun, on the other hand, is often late, so the Principal decides to expel him, but he was accepted again thanks to his Form Teacher who coincidentally happens to be their 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 Village garbage dump. The Chew siblings frantically search the garbage dump for her shoes, but only discover them as they are destroyed during a trade unionist riot against a police officer.
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 P.E. 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 labor, 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 the birth happened right on the same day Singapore became independent from Malaysia, and some time later, Beng Soon gives Kiat Kun and Seow Fang new pairs of shoes before departing for London, as a sign of reconciliation between him and the siblings.