Set in 1965 before Singapore gained independence from the Federation of Malaya, Homerun is the story of Ah Kun a 10-year-old school boy in an old village, and his younger sister, Seow Fang. Their mother is pregnant and is too weak to work; their father earns a meagre salary doing odd jobs and is behind on the rent.
One day, Ah Kun loses his sister's shoes while running an errand. Devastated, he asks her not to tell their poverty-stricken and frustrated parents. But how will she get to school without her shoes?
The siblings strike a deal. Seow Fang will wear Ah Kun's shoes to school in the morning, then run home so that Ah Kun can go to school in the afternoon. But Seow Fang finds getting back on time rather difficult, and Ah Kun is soon in trouble at school. Meanwhile, their father is looking for more lucrative work, and decides to try his luck as a deliveryman in the affluent quarter of the city.
Complications ensue until Ah Kun comes across a cross country race for school boys where the third prize is a pair of new shoes.
The story is set against a historical backdrop at the birth of a nation. While Ah Kun sees the solution of his problem in winning the race, uncertainty of the future looms in the minds of the people. Can they call this country their home?