Cauliflower and broccoli are important Cole vegetables grown worldwide for their health and food value. Glucosinolates, anthocyanin, β-carotene, ascorbic acids, and dietary minerals are the key health compounds in these vegetables. Evidence showed direct evolutionary lineage between broccoli and cauliflower, highlighting their use in breeding program. Both cauliflower and broccoli originated in Mediterranean region and further evolved in diverse ecotypes in different parts of the world through selections and mutations for adaptive changes. Inter- and intra-groups crossing and gene flow from wild-related species further contributed in evolution of diverse germplasm. Significant efforts were made to germplasm management and utilization for breeding against stresses and quality attributes. Development of tropical cauliflower and broccoli, introgression of quantitative trait loci (QTLs) from Brassica villosa for glucosinolates, and deploying sterile cytoplasm from different related wild species are some of the successful examples of utilizing diverse genepool for improvement of Cole crops. Further, biofortification of these crops using existing natural variability has great scope to contribute in human health. Global efforts on conservation and exchange are crucial for evolving new ecotypes particularly for climate resilient traits and biotic stresses tolerance to harness the benefits from rapid evolving habit of these crops.