Analyzing a crash using driving recorder data makes it possible to objectively examine factors contributing to the occurrence of the crash. In this study, car-to-cyclist crashes and near crashes recorded on cars equipped with advanced driving recorders were compared with each other in order to examine the factors that differentiate near crashes from crashes, as well as identify the causes of the crashes. Focusing on cases where the car and cyclist approached each other perpendicularly, the differences in the car's and cyclist's parameters such as velocity, distance and avoidance behavior were analyzed. The results show that car-to-cyclist crashes would not be avoidable when the car approaching the cyclist enters an area where the average deceleration required to stop the car is more than 0.45 G (4.4 m/s2). In order for this situation to occur, there are two types of cyclist crash scenarios. In the first scenario, the delay in the drivers’ reaction in activating the brakes is the main factor responsible for the crash. In this scenario, time-to-collision when the cyclist first appears in the video is more than 2.0 s. In the second scenario, the sudden appearance of a cyclist from behind an obstacle on the street is the factor responsible for the crash. In this case, the time-to-collision is less than 1.2 s, and the crash cannot be avoided even if the driver exhibited avoidance maneuvers.