Planting a cover crop between the main cropping seasons is an agricultural management measure with multiple potential benefits for sustainable food production. In the maize production system of the Netherlands, an effective establishment of a winter cover crop is important for reducing nitrogen leaching to groundwater. Cover crop establishment after maize cultivation is obliged by law for sandy soils and consequently implemented on nearly all maize fields, but the winter-time vegetative ground cover varies significantly between fields. The objectives of this study are to assess the variability in winter vegetative cover and evaluate to what extent this variability can be explained by the timing of cover crop establishment and weather conditions in two growing seasons (2017–2018). We used Sentinel-2 satellite imagery to construct NDVI time series for fields known to be cultivated with maize within the province of Overijssel. We fitted piecewise logistic functions to the time series in order to estimate cover crop sowing date and retrieve the fitted NDVI value for 1 December (NDVIDec). We used NDVIDec to represent the quality of cover crop establishment at the start of the winter season. The Sentinel-2 estimated sowing dates compared reasonably with ground reference data for eight fields (RMSE = 6.6 days). The two analysed years differed considerably, with 2018 being much drier and warmer during summer. This drought resulted in an earlier estimated cover crop sowing date (on average 19 days) and an NDVIDec value that was 0.2 higher than in 2017. Combining both years and all fields, we found that Sentinel-2 retrieved sowing dates could explain 55% of the NDVIDec variability. This corresponded to a positive relationship (R2 = 0.50) between NDVIDec and the cumulative growing degree days (GDD) between sowing date and 1 December until reaching 400 GDD. Based on cumulative GDD derived from two weather stations within Overijssel, we found that on average for the past three decades a sowing date of 19 September (± 7 days) ...