Precise and prompt predictions of crop yields are crucial for optimising farm management, post-harvest operations, and marketing strategies within the agricultural sector. While various machine learning approaches have been employed to forecast crop yield, their application to grain quality, particularly head rice yield (HRY), is less explored. This research collated crop-level HRY data across four seasons (2017/18–2020/21) from Australia’s rice-growing region. Models were developed using the XGBoost algorithm trained at varying time steps up to 16 weeks pre-harvest. The study compared the accuracy of models trained on datasets with climate data alone or paired with vegetative indices using two- and four-week aggregations. The results suggest that model accuracy increases as the harvest date approaches. The dataset combining climate and vegetative indices aggregated over two weeks surpassed industry benchmarks early in the season, achieving the highest accuracy two weeks before harvest (LCCC = 0.65; RMSE = 6.43). The analysis revealed that HRY correlates strongly with agroclimatic conditions nearer harvest, with the significance of vegetative indices-based features increasing as the season progresses. These features, indicative of crop and grain maturity, could aid growers in determining optimal harvest timing. This investigation offers valuable insights into grain quality forecasting, presenting a model adaptable to other regions with accessible climate and satellite data, consequently enhancing farm- and industry-level decision-making.