Although cycling offers many health and environmental benefits, it is not an activity free of injury risk. Increases in cycling popularity in the United States over the past 15 years have been paralleled by a 120% growth in cycling-related hospital admissions, with injuries to the head among the most common and debilitating injuries. Bicycle helmets can reduce head injury risk and are presently required to meet safety standard certification criteria specifying a minimal level of acceptable impact protection. However, the conditions surrounding cyclist head impacts are thought to be much more complex than the test conditions prescribed in standards and have important implications related to mechanisms of injury. The overarching aim of this dissertation was thus to investigate the protective capabilities of bicycle helmets in the context of real-world impact conditions and relevant head injury mechanisms. This aim was achieved through a series of studies, the objectives of which were to:​ compare helmet impact performance across standards impact testing and more realistic, oblique impact testing;​ to probe how changing boundary conditions of oblique impact testing may influence helmet test outcomes;​ to use this knowledge to inform the development of an objective helmet evaluation protocol reflective of realistic impact conditions and related head injury risks;​ and finally, to enhance the body of knowledge pertaining to cyclist head impact conditions via advanced helmet damage reconstruction techniques. The compilation of results across these studies serves to enhance cyclist safety by stimulating improved helmet evaluation and design while simultaneously providing objective, biomechanical data to consumers, enabling them to make safety-based purchasing decisions.