This work investigated the influence of crosswinds and leg positions on the aerodynamics of an articulated cycling mannequin on a track bicycle. Force, wake total pressure and wake velocity measurements were made in a low-speed sports wind tunnel of closed-circuit type. The freestream velocity and wheel speeds were kept at \(15\, \hbox {m/s}\) . The crank angle of the mannequin was varied across a pedal cycle. Yaw angles from \(0^{\circ }\) to \(20^{\circ }\) were examined. The experimental results reveal that the leg position significantly affects the aerodynamic performance of a cyclist. At high yaw angles, the aerodynamic drag on the cyclist showed noticeable deviations between most leg positions and their \(180^{\circ }\) -apart pairs. A wake analysis technique effectively captured the influence of leg positions on drag. The total pressure deficit contributes dominantly to the overall drag. The wake pressure contours demonstrate how leg-wheel interaction affects the total pressure distribution and drag under crosswinds. This study offers valuable insights into the flow behavior and drag generation around a cyclist with varying leg positions under crosswinds.