Surfing and skateboarding were primarily recreational sports before being thrust in the limelight of competition that culminated in their inclusion in the 2020 Tokyo Olympics. With their immense growth came increased propensity for musculoskeletal damage due to the performance of often aggressive airborne maneuvers. Direct trauma is the most common mechanism of injury in both sports. In surfing, the lower limbs are more often injured than the upper limbs, preferentially the rear extremities. Knee injuries like sprains, dislocations, and meniscal tears predominate. Contrary to surfing, skateboarding afflicts the upper extremities more than the lower extremities. Wrist and forearm trauma account for greater than half of all skateboarding injuries due to the participant falling on an outstretched arm. These sports will continue to grow in popularity, and knowing the common injury patterns can aid the radiologist in relevant and meaningful radiologic reporting and interpretation.