This work aims to compare and statistically analyze Normalized Difference Vegetation Index (NDVI) values provided by GreenSeeker handheld crop sensor measurements and calculate NDVI values derived from the MicaSense RedEdge-MX Dual Camera, to predict in-season winter wheat (Triticum aestivum L.) yield, improving a yield prediction model with cumulative growing degree days (CGDD) and days from sowing (DFS) data. The study area was located in Mosonmagyaróvár, Hungary. A small-scale field trial in winter wheat was constructed as a randomized block design including Environmental: N-135.3, P2O5-77.5, K2O-0; Balance: N-135.1, P2O5-91, K2O-0; Genezis: N-135, P2O5-75, K2O-45; and Control: N, P, K 0 kg/ha. The crop growth was monitored every second week between April and June 2022 and 2023, respectively. NDVI measurements recorded by GreenSeeker were taken at three pre-defined GPS points for each plot; NDVI values based on the MicaSense camera Red and NIR bands were calculated for the same points. Results showed a significant difference (p ≤ 0.05) between the Control and treated areas by GreenSeeker measurements and Micasense-based calculated NDVI values throughout the growing season, except for the heading stage. At the heading stage, significant differences could be measured by GreenSeeker. However, remotely sensed images did not show significant differences between the treated and Control parcels. Nevertheless, both sensors were found suitable for yield prediction, and 226 DAS was the most appropriate date for predicting winter wheat’s yield in treated plots based on NDVI values and meteorological data.