Head-to-vehicle contact boundary condition and criteria and corresponding thresholds of head injuries are crucial in evaluation of vehicle safety performance for pedestrian protection, which need a constantly updated understanding of pedestrian head kinematic response and injury risk in real-world collisions. Thus, the purpose of the current study is to investigate the characteristics of pedestrian head-to-vehicle contact boundary condition and pedestrian AIS3+ (Abbreviated Injury Scale) head injury risk as functions of kinematic-based criteria, including HIC (Head Injury Criterion), HIP (Head Impact Power), GAMBIT (Generalized Acceleration Model for Brain Injury Threshold), RIC (Rotational Injury Criterion), and BrIC (Brain Injury Criteria), in real-world collisions. To achieve this, 57 vehicle-to-pedestrian collision cases were employed, and a multi-body modeling approach was applied to reconstruct pedestrian kinematics in these real-world collisions. The results show that head-to-windscreen contacts are dominant in pedestrian collisions of the analysis sample and that head WAD (Wrap Around Distance) floats from 1.5 to 2.3 m, with a mean value of 1.84 m; 80% of cases have a head linear contact velocity below 45 km/h or an angular contact velocity less than 40 rad/s; pedestrian head linear contact velocity is on average 83 ± 23% of the vehicle impact velocity, while the head angular contact velocity (in rad/s) is on average 75 ± 25% of the vehicle impact velocity in km/h; 77% of cases have a head contact time in the range 50–140 ms, and negative and positive linear correlations are observed for the relationships between pedestrian head contact time and WAD/height ratio and vehicle impact velocity, respectively; 70% of cases have a head contact angle floating from 40° to 70°, with an average value of 53°; the pedestrian head contact angles on windscreens (average = 48°) are significantly lower than those on bonnets (average = 60°); the predicted thresholds of HIC, HIP, GAMBIT, RIC, BrIC2011, and BrIC2013 for a 50% probability of AIS3+ head injury risk are 1,300, 60 kW, 0.74, 1,470 × 104, 0.56, and 0.57, respectively. The findings of the current work could provide realistic reference for evaluation of vehicle safety performance focusing on pedestrian protection.