Head injuries are common for cyclists involved in collisions. Such collision scenarios result in a range of injuries, with different head impact speeds, angles, locations, or surfaces. A clear understanding of these collision characteristics is vital to design high fidelity test methods for evaluating the performance of helmets. We review literature detailing real-world cyclist collision scenarios and report on these key characteristics. Our review shows that helmeted cyclists have a considerable reduction in skull fracture and focal brain pathologies compared to non-helmeted cyclists, as well as a reduction in all brain pathologies. The considerable reduction in focal head pathologies is likely to be due to helmet standards mandating thresholds of linear acceleration. The less considerable reduction in diffuse brain injuries is likely to be due to the lack of monitoring head rotation in test methods. We performed a novel meta-analysis of the location of 1809 head impacts from ten studies. Most studies showed that the side and front regions are frequently impacted, with one large, contemporary study highlighting a high proportion of occipital impacts. Helmets frequently had impact locations low down near the rim line. The face is not well protected by most conventional bicycle helmets. Several papers determine head impact speed and angle from in-depth reconstructions and computer simulations. They report head impact speeds from 5 to 16 m/s, with a concentration around 5 to 8 m/s and higher speeds when there was another vehicle involved in the collision. Reported angles range from 10° to 80° to the normal, and are concentrated around 30°-50°. Our review also shows that in nearly 80% of the cases, the head impact is reported to be against a flat surface. This review highlights current gaps in data, and calls for more research and data to better inform improvements in testing methods of standards and rating schemes and raise helmet safety.