Laboratory-based biomechanical analyses of sport-relevant movements such as landing and cutting have classically been used to quantify kinematic and kinetic factors in the context of injury risk, which are then used to inform targeted interventions designed to improve risky movement patterns during sport. However, the noncontextual nature of standard assessments presents challenges for assessing sport-relevant skill transfer. To examine injury-risk biomechanical differences exhibited by athletes during a jump-landing task performed as part of both a standard biomechanical assessment and a simulated, sport-specific virtual reality (VR)-based assessment. Observational study. Medical center laboratory. Twenty-two female adolescent soccer athletes (age = 16.0 [1.4]y, height = 165.6 [4.9]cm, and weight = 60.2 [11.4]kg). The landing performance was analyzed for a drop vertical jump task and a VR-based, soccer-specific corner-kick scenario in which the athletes were required to jump to head a virtual soccer ball and land. Hip, knee, and ankle joint kinematic differences in the frontal and sagittal planes. Athletes exhibited reduced hip and ankle flexion, hip abduction, and frontal plane ankle excursion during landing in realistic sport scenario compared with the standard drop vertical jump task. VR-based assessments can provide a sport-specific context in which to assess biomechanical deficits that predispose athletes for lower-extremity injury and offer a promising approach to better evaluate skill transfer to sport that can guide future injury prevention efforts.