For different broccoli materials, it used to be necessary to manually plant in a large area for the investigation of flower ball information, and this method is susceptible to subjective influence, which is not only time-consuming and laborious but may also cause some damage to the broccoli in the process of investigation. Therefore, the rapid and nondestructive monitoring of flower heads is key to acquiring high-throughput phenotypic information on broccoli crops. In this study, we used an unmanned aerial vehicle (UAV) to acquire hundreds of images of field-grown broccoli to evaluate their flower head development rate and sizes during growth. First, YOLOv5 and YOLOv8 were used to complete the position detection and counting statistics at the seedling and heading stages. Then, UNet, PSPNet, DeepLabv3+, and SC-DeepLabv3+ were used to segment the flower heads in the images. The improved SC-DeepLabv3+ model excelled in segmenting flower heads, showing Precision, reconciled mean F1-score, mean intersection over union, and mean pixel accuracy values of 93.66%, 95.24%, 91.47%, and 97.24%, respectively, which were 0.57, 1.12, 1.16, and 1.70 percentage points higher than the respective values achieved with the DeepLabv3+ model. Flower head sizes were predicted on the basis of the pixel value of individual flower heads and ground sampling distance, yielding predictions with an R2 value of 0.67 and root-mean-squared error of 1.81 cm. Therefore, the development rate and sizes of broccoli flower heads during growth were successively estimated and calculated. Compared with the existing technology, it greatly improves work efficiency and can help to obtain timely information on crop growth in the field. Our methodology provides a convenient, fast, and reliable way for investigating field traits in broccoli breeding.