Hailstorms can be responsible for significant economic loss to the agricultural sector in Alberta, Canada. Foliar applications of certain fungicides and nutrient blends have been advocated to promote recovery and yield of hail-damaged crops. Proper understanding of different crop and hail-related factors is required for an accurate assessment of hail damage to crops and for evaluations of hail-recovery product claims. This study was undertaken at three locations in Alberta during three growing seasons (2016–2018) to determine the effects of two levels of simulated hail severity at three different crop developmental stages, including the early growth (BBCH 30 for wheat; BBCH 14–16 for pulses), mid-growth (BBCH 39 for wheat; BBCH 60 for pulses), and late growth (BBCH 60 for wheat; BBCH 71 for pulses) stages. Plant growth and yield parameters of wheat (Triticum aestivum L.), field pea (Pisum sativum L.), and dry bean (Phaseolus vulgaris L.) crops were measured. Simulated hail damage led to reductions in height, biomass, NDVI, grain yield, and kernel weight of all three crops. Average yield decreased by 24% and 35% for wheat, 17% and 35% for dry beans, and 37% and 45% for field peas for light and heavy hail severity, respectively. Hail timing was a critical factor influencing the extent of crop damage, with hail damage during the early growth stage leading to a lesser yield reduction compared with hail damage at the mid-growth and late growth stages. Fungicides and nutrient blends applications did not significantly improve crop recovery, grain yield, or kernel weight for any of the crops in this study.