Knowing the phenology, production, and fruit quality of blackberry cultivars grown in greenhouses enables growers to develop and/or improve assertive orchard management. The aim of this study was to investigate whether phenology, production, and fruit quality differ among blackberry cultivars grown under greenhouse. The treatments were four blackberry cultivars (‘BRS Cainguá’, ‘BRS Tupy’, ‘BRS Xavante’, and ‘BRS Xingu’), arranged in a randomized block design, with four replications and three plants per plot. Phenology, production, and fruit quality were assessed. ‘BRS Xingu’ had an earlier start than all the phenological stages assessed, proving to be the earliest to achieve fruit harvest stage. ‘BRS Cainguá’ was the latest to harvest. ‘BRS Xingu’ showed the highest total production values, followed by ‘BRS Cainguá’, with the largest longitudinal diameter, and ‘BRS Tupy’, with the largest transverse diameter. Fruit quality was not influenced by the cultivars. In conclusion, the four blackberry cultivars differ in terms of phenology and fruit production potential under greenhouse. This allows production to be staggered around 15 days in terms of the start and end of the harvest.