We suspected that the observed inconsistency of sex differences in drop-landing motor skills might be due to the confounding factor of prior experience. Thus, in this study, we explored the role of experience in shaping male and female surfboard riders’ motor skill kinematics during drop landings while surfboard riding. We recruited 42 participants (21 females and 21 males) from three groups of surfing experience levels (competitive surfers, recreational surfers, and nonsurfers), each equally comprising seven males and seven females. Sagittal plane kinematics and vertical ground reaction force data were collected from all participants during a laboratory-based 60-cm drop-landing task. Knee flexion and ankle dorsiflexion at initial ground contact were greater among male participants, independent of experience level. In both sexes, greater range of motion at these joints was related to greater experience. Recreational female surfers landed in a more upright posture with more extended ankle and knee angles and less ankle dorsiflexion at the end of landing than participants in all other groups. We discuss our results in the context of possible remaining experience differences between male and female participants despite being grouped in the same experience levels in our study, individualized motor patterns that may still achieve similar success, and a need for continued research.