This paper analyzes the field performance of two cup anemometers installed in Zaragoza (Spain). Data acquired over almost three years, from January 2015 to December 2017, were analyzed. The effect of the different variables (wind speed, temperature, harmonics, wind speed variations, etc.) on two cup anemometers was studied. Data analysis was performed with ROOT, an open-source scientific software toolkit developed by CERN (Conseil Européen pour la Recherche Nucléaire) for the study of particle physics. The effects of temperature, wind speed, and wind dispersion (as a first approximation to atmospheric turbulence) on the first and third harmonics of the anemometers’ rotation speed (i.e., the anemometers’ output signature) were studied together with their evolution throughout the measurement period. The results are consistent with previous studies on the influence of velocity, turbulence, and temperature on the anemometer performance. Although more research is needed to assess the effect of the anemometer wear and tear degradation on the harmonic response of the rotor’s angular speed, the results show the impact of a recalibration on the performance of an anemometer by comparing this performance with that of a second anemometer.