The accumulated damage from elephant weevil larvae, Orthorhinus cylindrirostris (F.) (Coleoptera: Curculionidae), reduces blueberry yield and shortens the productive lifespan of blueberry plants by several years. Selective breeding to develop pest-resistant blueberry cultivars is a possible control option, but the relationship between O. cylindrirostris populations, plant damage, and blueberry yield has not been described. A field survey of 17 blueberry cultivars was conducted on a commercial farm to measure O. cylindrirostris populations (emergence holes and adult numbers) and yield from plants of different ages (2–12 yr). Blueberry plants accumulated damage over time, that is, older plants tended to have more O. cylindrirostris emergence holes than younger plants. All cultivars received some level of O. cylindrirostris attack but this did not always lead to yield losses. Newer cultivars that have been in production since 2000 were less susceptible to O. cylindrirostris than older cultivars. Removal of highly susceptible cultivars from commercial blueberry farms may reduce O. cylindrirostris populations. There is potential for selective breeding to increase plant resistance to O. cylindrirostris if the specific resistance mechanisms can be identified in blueberry.