In-season crop growth and yield prediction at high spatial resolution are essential for informing decision-making for precise crop management, logistics and market planning in horticultural crop production. This research aimed to establish a plant-level cabbage yield prediction system by assimilating the leaf area index (LAI) estimated from UAV imagery and a segmentation model into a crop simulation model, the WOrld FOod STudies (WOFOST). The data assimilation approach was applied for one cultivar in five fields and for another cultivar in three fields to assess the yield prediction accuracy and robustness. The results showed that the root mean square error (RMSE) in the prediction of cabbage yield ranged from 1,314 to 2,532 kg ha–1 (15.8–30.9% of the relative RMSE). Parameter optimisation via data assimilation revealed that the reduction factor in the gross assimilation rate was consistently attributed to a primary yield-limiting factor. This research further explored the effect of reducing the number of LAI observations on the data assimilation performance. The RMSE of yield was only 107 kg ha–1 higher in the four LAI observations obtained from the early to mid-growing season than for the nine LAI observations over the entire growing season for cultivar ‘TCA 422’. These results highlighted the great possibility of assimilating UAV-derived LAI data into crop simulation models for plant-level cabbage yield prediction even with LAI observations only in the early and mid-growing seasons.