Plantar pressure data were recorded in two different shoe types to determine the effect of cycling shoe stiffness on peak plantar forefoot pressure in cyclists. Two pairs of shoes of the same size and manufacturer, identical except for outsole material and stiffness, were tested. Shoe stiffness measurements were collected under controlled conditions and in two different configurations using a dynamic hydraulic tensile testing machine. Measurements of plantar pressure were done using Pedar capacitive-based sensor insoles while subjects pedaled in a seated position at a controlled power output. Power output was set at a constant value of 400 W across all subjects by a magnetic resistance trainer unit. The pressure distribution in carbon-fiber-composite shoes during cycling was compared to cycling shoes made with plastic soles. Carbon fiber shoes presented stiffness values 42% and 550% higher than plastic shoes in longitudinal bending and three-point bending, respectively. The shoes made with carbon fiber produced peak plantar pressures 18% higher than those of plastic design (121 kPa vs. 103 kPa, p = .005). Competitive or professional cyclists suffering from metatarsalgia or ischemia should be especially careful when using carbon fiber cycling shoes because the shoes increase peak plantar pressure, which may aggravate these foot conditions.