The environments where the progenitors are grown have the potential to affect the expression of traits in their offspring. Currently, there are various hypotheses regarding the evolutionary and ecological importance of stress memory effects. There is uncertainty regarding its occurrence, persistence, predictability, and adaptive value. In this study, fifteen winter wheat cultivars were grown under drought and well-watered (control) treatments for two seasons to produce seeds with all possible combinations of drought exposure histories. A comprehensive analysis to estimate transgenerational (grandparental effects), intergenerational (parental effects), and their combined memory effects on offspring traits under both control and drought moisture treatments was performed. There were significant memory effects in most of the evaluated traits ranging from +787% to -39.0% changes in both seed quality and plant traits. The expression of stress memory was highly dependent on generation and number of exposures, trait and season. Under drought treatment, the combination of grandparental and parental stress memories was additive in all traits, but their strength were variable when considered separately. Stress memory enhanced the performance of offspring under similar stressful conditions: increased plant height, above-ground biomass, number of grains per plant, grain weight per plant and water potential. This study offers valuable new insights into the occurrence of drought stress memory, the complexities of the effects, possible physiological and metabolic alterations explaining the detected differences, and impacts towards a clearer understanding of their generation and context-dependency. This article is protected by copyright. All rights reserved.