ERA5 reanalysis output is compared to WindSat measurements over cyclones at Southern Hemisphere mid- to high-latitudes. WindSat provides an independent measure of how well ERA5 represents cyclones, as WindSat is not assimilated into ERA5. We implement a tracking scheme to identify cyclone centres and tracks, before using cyclone composites to match concurrent data in ERA5 and WindSat. We find that both ERA5 and WindSat show comparable spatial structures for low level wind speed, total column water vapour, cloud liquid water and precipitation. Compared to WindSat, ERA5 underestimates total column water vapour by up to 5\% and cloud liquid water by up to 40\%. ERA5 underestimates precipitation in the warm sector by up to 15\%, but overestimates in the cold sector by up to 60\%. Similar biases in ERA5 are seen when comparing to AMSR-E data, even though AMSR-E radiances are assimilated into ERA5. Comparing ERA5 and WindSat across the cyclone lifecycle, a strong correlation is seen across the cyclone as it deepens and reaches peak intensity, before slightly declining as the cyclone decays. In the cold sector ERA5 shows underestimation of cloud liquid water, yet overestimates precipitation at all lifecycle stages. However, in the warm sector precipitation is underestimated. This potentially suggests the presence of biases within the ERA5 parameterisations of cloud and precipitation causing a disconnect between the two. Despite this, ERA5 shows strong correlation with WindSat and determines cyclone structure well across the cyclone lifecycle, showing its value for use in cyclone compositing analysis.