This study evaluates a temporally dense VV-polarized Sentinel-1 C-band backscatter time series (revisit time of 1.5 days) for wheat fields near Munich (Germany). A dense time series consisting of images from different orbits (varying acquisition) is analyzed, and Radiative Transfer (RT)-based model combinations are adapted and evaluated with the use of radar backscatter. The model shortcomings are related to scattering mechanism changes throughout the growth period with the use of polarimetric decomposition. Furthermore, changes in the RT modeled backscatter results with spatial aggregation from the pixel to field scales are quantified and related to the sensitivity of the RT models, and their soil moisture output are quantified and related to changes in backscatter. Therefore, various (sub)sets of the dense Sentinel-1 time series are analyzed to relate and quantify the impact of the abovementioned points on the modeling results. The results indicate that the incidence angle is the main driver for backscatter differences between consecutive acquisitions with various recording scenarios. The influence of changing azimuth angles was found to be negligible. Further analyses of polarimetric entropy and scattering alpha angle using a dual polarimetric eigen-based decomposition show that scattering mechanisms change over time. The patterns analyzed in the entropy-alpha space indicate that scattering mechanism changes are mainly driven by the incidence angle and not by the azimuth angle. Besides the analysis of differences within the Sentinel-1 data, we analyze the capability of RT model approaches to capture the observed Sentinel-1 backscatter changes due to various acquisition geometries. For this, the surface models “Oh92” or “IEM_B” (Baghdadi’s version of the Integral Equation Method) are coupled with the canopy model “SSRT” (Single Scattering Radiative Transfer). To resolve the shortcomings of the RT model setup in handling varying incidence angles and therefore the backscatter changes observed between consecutive time steps of a dense winter wheat time series, an empirical calibration parameter (coef) influencing the transmissivity (T) is introduced. The results show that shortcomings of simplified RT model architectures caused by handling time series consisting of images with varied incidence angles can be at least partially compensated by including a calibration coefficient to parameterize the modeled transmissivity for the varying incidence angle scenarios individually.