Almond is an important tree nut crop worldwide, and planted areas have been increasing year after year. While self-fertility is one of the key factors when it comes to improved almond productivity of new cultivars, yield is also affected by the number of flowers produced, pollination, fruit set, fruit drop, and fruit weight. Almond fruit drop patterns of 20 Mediterranean almond cultivars were studied over three years. In addition, fruit drop patterns of two scion cultivars ‘Marinada’ and ‘Vairo’ budded onto eight to 10 different rootstocks managed with three different pruning strategies were studied for two years. Cumulative flower and fruit drop ranged from 50% to 90% among cultivars and treatments, and there were up to four fruit drop events during the growing season, the main one occurring from 20–60 days from full bloom (DFFB). Subsequent drops were at 100 DFFB, 120–140 DFFB, and the last one at 160–180 DFFB. The later drops were less apparent. In general, about half of the cumulative drop was comprised of buds and flowers, and the remaining percentage was fruit that dropped 20 or more days after full bloom. Furthermore, different fruit drop patterns were observed depending on the cultivar. For late- and extra-late flowering cultivars, cumulative fruit drop began to decrease earlier, with most of the drops occurred already at full bloom, whereas the opposite was observed for the early flowering cultivars. Rootstocks also had an important effect on the fruit drop pattern, with different effects depending on the scion cultivar. Tree management, such as type of pruning, also had an important effect on the rate of fruit drop and cumulative drop. Therefore, each combination of cultivar × rootstock × pruning type will require different strategies in order to reduce the fruit drop and optimize crop loads.