Interactions between soil moisture and terrestrial evaporation affect water cycle behaviour and responses between the land surface and the atmosphere across scales. With strong heterogeneities at the land surface, the inherent spatial variability in soil moisture makes its representation via point-scale measurements challenging, resulting in scale-mismatch when compared to coarser-resolution satellite-based soil moisture or evaporation estimates. The Cosmic Ray Soil Moisture Observing System (COSMOS) was developed to address such issues in the measurement and representation of soil moisture at intermediate scales. Here we present an examination of the links observed between COSMOS soil moisture retrievals and evaporation estimates over a pasture in the semi-arid central-west region of New South Wales, Australia. The COSMOS soil moisture product was compared to evaporation derived from three distinct approaches, including the Priestley-Taylor (PT-JPL), Penman-Monteith (PM-Mu) and Surface Energy Balance System (SEBS) models, driven by forcing data from local meteorological station data and remote sensing retrievals from the Moderate Resolution Imaging Spectroradiometer (MODIS) sensor. Pearson’s Correlations, Quantile-Quantile (Q-Q) plots, and Analysis of Variance (ANOVA) were used to qualitatively and quantitatively evaluate the temporal distributions of soil moisture and evaporation over the study site. The relationships were examined against nearly two years of observation data, as well as for different seasons and for defined periods of analysis. Results highlight that while direct correlations of raw data were not particularly instructive, the Q-Q plots and ANOVA illustrate that the root-zone soil moisture represented by the COSMOS measurements and the modelled evaporation estimates reflect similar distributions under most meteorological conditions. The PT-JPL and PM-Mu model estimates performed contrary to expectation when high soil moisture and cold temperatures were present, while SEBS model estimates displayed a disconnect from the soil moisture distribution in summers with long dry spells. Importantly, no single evaporation model matched the statistical distribution of the measured soil moisture for the entire period, highlighting the challenges in effectively capturing evaporative flux response within changing landscapes.