Understanding the performance of strawberry cultivars in response to the evolving environment and growth medium is a key factor in choosing materials with the aptitude to serve the consumer market. Here, we investigated whether strawberry cultivars in soilless cultivation and greenhouse differ in their agronomic potential. We have studied seven cultivars in an experiment designed in randomized blocks, with four replications. We used analysis of variance and multivariate to examine production attributes, the chemical quality of fruits, and their phytochemical profile. Among the seven cultivars, three heterogeneous groups were formed, gathering the materials mainly due to the similarity in terms of the content of total polyphenols (TPO) and average fresh fruit mass (AFFM). ‘Aromas’ produced the greatest number of strawberries. ‘Fronteras’ and ‘Monterey’, in turn, were the most productive cultivars, and ‘Albion’ and ‘Fronteras’ produced the largest fruits. ‘Albion’ produced the sweetest and tastiest fruits, with an adequate relationship between sugar and acidity. ‘Camino Real’ produced fruits with higher phytochemical content. We conclude that the seven strawberry cultivars in soilless cultivation and greenhouse have contrasting agronomic potential, which indicates that the producers can establish their crops with different materials. We suggest the use of ‘Fronteras’ to obtain greater yield and fruit size, ‘Albion’ to producers looking to grow sweeter and tastier fruits, and ‘Camino Real’ to obtain strawberries rich in secondary metabolites.