(1) Background: Notio calculates coefficient of drag area (CDA) considering dynamic pressure data calculated by an integrated Pitot-static tube. Therefore, this study aimed to evaluate the validity and reliability of Pitot-static tube calculations through wind speed (WS) data, against a hot-wire anemometer (HWA). (2) A total of 60 recordings were made, lasting 30 seconds each, in a closed-circuit wind tunnel at 4 different WS (≈30 to ≈60km/h), and at five different yaw angles (0º to 20º). (3) Results: Notio showed WS 6.44% higher than HWA. The calibration process recommended by the Notio manufacturer reduced the differences to a non-significant 0.76%. Comparison of the WS of Notio calibrated and HWA only showed significant differences in the WS group of ≈60 km/h. There were no significant differences in the comparison of yaw angles groups. The reliability of Notio was worse than that of the HWA. (4) Conclusions: Notio calibrated at a speed close to its use, allows reliable and accurate calculation of WS over a wide range of yaw angles under controlled wind tunnel conditions without the presence of a cyclist and bike. However, due to the influence of WS on aerodynamic drag, small errors in WS could translate into considerable values of CDA for cycling performance.