Roselle (Hibiscus sabdariffa L.) is recognized as a valuable food crop due to its nutraceutical potential, rich pigment content, and medicinal properties. However, there is limited information on planting dates and suitable genotypes for roselle cultivation in arid and semi-arid regions. The objective of this field study was to investigate the influence of five planting dates (March, April,May, June, and July) onmorphological and phytochemical characteristics of different roselle genotypes. Among genotypes, eight (Jiroft, Dalgan, Bampoor, Iranshahr, Nikshahr, Roodbar, Saravan, and Qaleganj) were Iranian landraces, and HA and HS-24 were originated from Ghana and Bangladesh, respectively. Planting date significantly influenced the number of branches, bolls and seeds per plant, sepal fresh weight, calyx and biomass yields, and harvest index in tested roselle landraces. The greatest morphological growth, fresh sepal weight (50.6 g plant−1) and calyx yield (1519 kg ha−1) were observedwith the roselle planted in early May. Moreover, amounts of chlorophyll, flavonoids and antioxidant remained higher in rosellewhen planted between April–May. The number of branches/plant was found to be an important determinant of calyx yield (r=0.707) in roselle. Dalgan resulted in the greatest growth and yields within a comparatively shorter period of time compared to other tested landraces. Both principal component analysis (PCA) and cluster analysis also indicated that Dalgan landrace possessed most suitable morphological and phytochemical traits among tested landraces, and therefore, it could be planted adopted for extensive cultivation settings in the arid and semi-arid regions.