Forests’ ecosystems are an essential part of the global carbon cycle with vast carbon storage potential. These systems are currently under external pressures showing increasing change due to climate change. A better understanding of the biophysical properties of forests is, therefore, of paramount importance for research and monitoring purposes. While there are many biophysical properties, the focus of this study is on the in-depth analysis of the connection between the C-band Copernicus Sentinel-1 SAR backscatter and evapotranspiration (ET) estimates based on in situ meteorological data and the FAO-based Penman–Monteith equation as well as the well-established global terrestrial ET product from the Terra and Aqua MODIS sensors. The analysis was performed in the Free State of Thuringia, central Germany, over coniferous forests within an area of 2452 km², considering a 5-year time series (June 2016–July 2021) of 6- to 12-day Sentinel-1 backscatter acquisitions/observations, daily in situ meteorological measurements of four weather stations as well as an 8-day composite of ET products of the MODIS sensors. Correlation analyses of the three datasets were implemented independently for each of the microwave sensor’s acquisition parameters, ascending and descending overpass direction and co- or cross-polarization, investigating different time series seasonality filters. The Sentinel-1 backscatter and both ET time series datasets show a similar multiannual seasonally fluctuating behavior with increasing values in the spring, peaks in the summer, decreases in the autumn and troughs in the winter months. The backscatter difference between summer and winter reaches over 1.5 dB, while the evapotranspiration difference reaches 8 mm/day for the in situ measurements and 300 kg/m²/8-day for the MODIS product. The best correlation between the Sentinel-1 backscatter and both ET products is achieved in the ascending overpass direction, with datasets acquired in the late afternoon, and reaches an R²-value of over 0.8. The correlation for the descending overpass direction reaches values of up to 0.6. These results suggest that the SAR backscatter signal of coniferous forests is sensitive to the biophysical property evapotranspiration under some scenarios.