Recently, due to evolution of equipment and techniques, ordinary-level windsurfers can attempt acrobatic activities that previously only high-level windsurfers could perform in stormy conditions. Moreover, many difficult aerial tricks have been developed by high-level windsurfers. Synchronously, “foot strap injuries” have increased, which affect the knee, ankle, and foot by twisting loads because the foot is unable to be released from the foot strap. Here we report three Lisfranc ligament injuries in windsurfers that had not been diagnosed appropriately at another medical institution. The cases of two professional, and one amateur windsurfer, all of whom sustained a sprain to the anterior foot when they failed to land properly following an aerial trick or during wave riding, are reported in this publication. Weightbearing anterior to posterior (AP) view radiographs were an important tool for the diagnosis of these Lisfranc ligament injuries which can easily be missed on nonweightbearing films. Surgical treatment was chosen for two cases and conservative treatment was chosen for the other. To allow the windsurfers to return successfully to competition, we devised a special cork insole inside a marine boot called the “Ninja.” Lisfranc Ligament injuries should be suspected as there are frequent foot injuries in windsurfers, and adequate treatment can enable the patients to return to competition successfully.