The results of several research campaigns investigating cup anemometer performance carried out since 2008 at the IDR/UPM Institute are included in the present paper. Several analysis of large series of calibrations were done by studying the effect of the rotor's geometry, climatic conditions during calibration, and anemometers' ageing. More specific testing campaigns were done regarding the cup anemometer rotor aerodynamics, and the anemometer signals. The effect of the rotor's geometry on the cup anemometer transfer function has been investigated experimentally and analytically. The analysis of the anemometer's output signal as a way of monitoring the anemometer status is revealed as a promising procedure for detecting anomalies.