Global warming affects rice crop production, causing deterioration of rice grain quality. This study used C-band microwave images taken by the Sentinel-1 satellites to monitor rice crop growth with the aim to understand microwave backscatter behavior, focusing on decreases in panicle water contents with ripening, which affect C-band backscatter. Time-series changes illustrated a similar tendency across all four analysis years, showing that VV/VH ratio at an incidence angle of 45–46° stopped decreasing to be stable over the reproductive and ripening periods due to reductions in the panicle water content that allowed for greater microwave penetration into the canopy, thereby increasing panicle-related backscatter. Furthermore, multivariate regression analysis combined with field observations showed that VV and VH with the shallow incidence angles were significantly negatively correlated with panicle water content, which well demonstrated backscatter increases with plant senescence. Furthermore, it was observed that backscatter behaviors were highly consistent with changes in crop phenology and surface condition. Accordingly, Sentinel-1 images with shallow incidence angles and high revisit observation capabilities offer a strong potential for estimating panicle water content. Therefore, it seems reasonable to conclude that C-band SAR data is capable of retrieving grain filling conditions to estimate proper harvesting time.