Amateur or non-competitive cycling is one of the most popular and growing sports, and the repetitive nature of this sport, combined with a cleat position that is too far forward, often leads to peripheral ischemia or pressure, which can cause pain at the metatarsal level due to the nerve and vascular structures present at this level, according to several authors. This clinical series describes the work done to reduce pain in 21 cyclists who reported foot pain/discomfort exclusively during pedaling. To exclude different causes of pain, other than the position of the cleat, the cyclists received biomechanical assessments using an indoor bike smart trainer and a 2D motion capture system. The pain was found to be associated with the incorrect positioning of the shoe cleats, which were generally positioned at the level of the phalanges and, according to our hypothesis, in a significantly forward position. Our intervention was to move the cleat back under the metatarsal head in all the cyclists examined. After five cycling sessions, feedback showed significant improvements. The authors were aware of some limitations, such as the small number of subjects studied, the different types of cleats used by different cyclists, and the lack of information on cadence. However, the overall data collected during the study showed a significant improvement of 5 points on the Numeric Pain Rating Scale (NPRS) after treatment. This clinical series supports the hypothesis that cleat retraction improves foot pain in cyclists, but further studies are needed to better characterize and understand the mechanism underlying the development of pain. More methodologically sound studies are needed. The current clinical series is the first of its kind to describe an initial method of reducing metatarsal pain in cyclists.