Retention of cotton, Gossypium hirsutum L., bolls and squares (referred to as fruit retention), boll damage, and resulting lint and seed weight loss were assessed when two (2010) and three (2011) age classes of sympodial fruiting branches with different ages of squares and bolls where exposed to verde plant bug, Creontiades signatus Distant (Hemiptera: Miridae), in cages in the field. An increasing trend was observed in fruit retention from the youngest to the oldest branch age treatment for both years, and the effect was primarily determined by the age of the fruiting body. Low fruit retention (<20%) was seen in young bolls <7 days old in the first two fruiting positions from the main stem compared with >80% retention in checks not exposed to verde plant bug. In infested cages, fruit retention of young bolls was significantly less (P = 0.016) than older bolls and squares 2–3 days before bloom or younger. Similar to fruit retention results, damage of harvested bolls and lint and seed weight (using zero for abscised fruit) differed among the age of the fruiting body primarily for fruiting positions one (2010 and 2011) and two (2011) (P < 0.0001). The first two fruiting positions were the main contributors to plant productivity differences in lint and seed weight. Overall, verde plant bugs given a feeding choice reduced fruit retention in young bolls <7 days old, damaged retained bolls <11 days old, and larger bolls and young squares at least 2–3 days from bloom incurred significantly less abscission and damage. These results supported the interpretation that less fruit retention and more damage of young bolls justified a focus on protecting young bolls in a pest management program, especially during early to peak bloom when young bolls are abundant.