Cropping practices used in banana production are currently shifting towards agroecological management, but the resulting performances of Cavendish banana cultivars need to be reassessed. This study aimed to gain insight into the impacts of the cultivar and cropping environment on the agronomic performances—in terms of agronomic traits—on a range of Cavendish cultivars. Twelve phenotypically contrasted cultivars were studied in five experimental cropping conditions in Guadeloupe. These conditions differed in terms of their black sigatoka management, fertilisation level and weed management strategy. The cultivar agronomic performances were assessed according to eight agronomic traits related to plant morphology and yield. Our results showed that the cropping conditions (environment) had a greater effect than the cultivars (genotype) on agronomic traits, while their interaction (GEI) had almost no effect. The potential nutritional limitation times (vegetative vs reproductive phases) also impacted the agronomic traits, in accordance with yield build-up components in banana plants. Moreover, there was a positive correlation between all traits, with no trade-offs. Finally, our findings showed that while cultivars tolerant to sub-optimal cropping conditions are essential, the system design and cropping practices are crucial to limit and buffer nutritional stresses and their impacts on banana growth and yield. Based on these results, we propose prospects for the design of cropping systems to improve productivity despite limiting growing environments.