Although the boll weevil (BW), Anthonomus grandis grandis (Coleoptera: Curculionidae) has been attributed to the significant losses caused to cotton yield in the Americas, the categorization as a quarentenary pest in places where it is still not occurring has increased its relevance worldwide. In areas where it is widespread, pest suppression relies on many broad-spectrum insecticide applications. However, other control tactics are sought. Considering that early-flowering cultivars escape from boll weevil infestation, we investigated if three different planting dates (November, December, and January) could alter the plant life cycle, allowing the plants to escape from boll weevil infestation. Field trials were run in two seasons (2014/2015 and 2017/2018), and variables (days required to reach each flowering stage, fruiting plant structures—undamaged and damaged by the BW, and totals—number of boll weevils on plants and that had emerged from fallen structures on the ground) were assessed over 29 and 33 weeks, respectively. Based on the number of days required to initiate and terminate the flowering stage, the time to reach the economic threshold (ET), the number of undamaged, damaged, and the total reproductive structures, we concluded that planting dates in December for the Central Cerrado of Brazil should be preferred over the other two tested dates. Cultivations run at this planting date, anticipating the flowering period initiation and termination, reduced infested flowering structures, and delayed the decision making to control the pest, when compared to the other two planting dates.