The idea that the universe is a deterministic system has been historically present in both Eastern and Western philosophy. According to this view, every event is determined by natural laws and occurs within an unbroken chain of causes and effects. Within this chain, is there room for human choice? Indeed, when we consider Determinism, the issues of Chance and Free Will emerge as related concerns. The aim of this presentation is to explore this core theme as reflected in selected poems and a short story by Jorge Luis Borges, in Dostoievsky’s novel Crime and Punishment and in Woody Allen’s film Match Point. The chosen poems by Borges contain philosophical echoes and involve a concern with finding one’s identity within a deterministic framework. The short story chosen to illustrate this theme, “El Muerto”, narrates a series of loosely connected acts leading to a tragic end which is known by the reader from the very start. A glimpse at Fyodor Dostoevsky’s Crime and Punishment will provide rich explorations in human nature, crime, religion and the role of fate and self-determination in the course of human life. To conclude, selected scenes from Woody Allen’s Match Point will contribute to rounding off the theme. When including Crime and Punishment as a motif, Allen appears to oppose Dostoievsky’s moral view through a skeptical, pessimistic outlook, one where there is no room for guilt or redemption.