Vulnerable road users (VRUs) are frequently involved in road traffic crashes worldwide, and the most serious consequences often occur in collisions with motor vehicles. Countermeasures such as advanced driver assistance systems (ADASs) for have been developed and implemented in vehicles to reduce these crashes. Estimations of the effectiveness of these systems are so far dominated by prospective studies; only a few analyze real-world crash data. The objective of this study was to estimate the crash-reducing effects of the VRU ADAS systems in car-to-pedestrian and car-to-bicycle crashes involving Volvo cars in Sweden using real-world crash data. Car-to-pedestrian and car-to-bicycle collisions across Sweden from 2015–2020 (in which the car was moving forward) were identified using insurance claims at If P&C insurance. Volvo car models with ADAS VRU and comparable Volvo models without the system were selected. Poisson regression was used to estimate the effect of the VRU ADAS on the crash rate, calculated per insured vehicle-years. For the second generation of VRU ADAS, the straight crossing path (SCP) and parallel (Longitudinal) crash rate was found to be 12% less in car-to-pedestrian/bicycle crashes—23% less in car-to-pedestrian crashes and 6% less in car-to-bicycle crashes. However, no results were statistically significant. There was no difference in crash rates when evaluating all crash situations where the car was moving forward. The limitation of this study is the low number of crashes. Reducing crashes and injuries in vehicle-to-VRU conflicts is of utmost importance for fulfilling the aims highlighted in Agenda 2030. Improving ADAS to better avoid collisions with pedestrians and cyclists has the potential to greatly improve traffic safety; future generations of the system are expected to increase VRU safety benefits. Measuring ADAS effects in real-world traffic and interpreting and relating the results are essential to ensure that future systems improve VRU safety.