Cycling accidents are the leading cause of sports-related head injuries in the US. Conventional bicycle helmets typically consist of polycarbonate shell over Expanded Polystyrene (EPS) foam and are tested with drop tests to evaluate a helmet’s ability to reduce head kinematics. Within the last decade, novel helmet technologies have been proposed to mitigate brain injuries during bicycle accidents, which necessitates the evaluation of their effectiveness in impact testing as compared to conventional helmets. In this paper, we reviewed the literature to collect and analyze the kinematic data of drop test experiments carried out on helmets with different technologies. In order to provide a fair comparison across different types of tests, we clustered the datasets with respect to their normal impact velocities, impact angular momentum, and the type of neck apparatus. When we analyzed the data based on impact velocity and angular momentum clusters, we found that the bicycle helmets that used rotation damping based technology, namely MIPS, had significantly lower peak rotational acceleration (PRA) and Generalized Acceleration Model for Brain Injury Threshold (GAMBIT) as compared to the conventional EPS liner helmets (p < 0.01). SPIN helmets had a superior performance in PRA compared to conventional helmets (p < 0.05) in the impact angular momentum clustered group, but not in the impact-velocity clustered comparisons. We also analyzed other recently developed helmets that primarily use collapsible structures in their liners, such as WaveCel and Koroyd. In both of the impact velocity and angular momentum groups, helmets based on the WaveCel technology had significantly lower peak linear acceleration (PLA), PRA, and GAMBIT at low impact velocities as compared to the conventional helmets, respectively (p < 0.05). The protective gear with the airbag technology, namely Hövding, also performed significantly better compared to the conventional helmets in the analyzed kinematic-based injury metrics (p < 0.001), possibly due to its advantage in helmet size and stiffness. We also observed that the differences in the kinematic datasets strongly depend on the type of neck apparatus. Our findings highlight the importance and benefits of developing new technologies and impact testing standards for bicycle helmet designs for better prevention of traumatic brain injury (TBI).