The genetic diversity present in the breeding programs of southeast Europe was assessed in a set of 114 winter wheat (Triticum aestivum L.) cultivars using AFLP and SSR markers. The average genetic diversity characterised with the Jaccard's distance coefficient was 0.605 with an interval of 0.053 and 0.889. The wheat cultivars originating from the four countries differed from each other in their clustering patterns, including the numbers of clusters and the most prevalent cluster, which was breeding program-specific. Hungarian and Romanian cultivars showed closer relationships, and Serbian and Macedonian cultivars grouped together more frequently. The phenotypic variability of the same cultivars was assessed under diverse ecological conditions of the four growing sites, measuring the disease resistance against two foliar diseases, and several agronomic traits. Of the phenotypic traits, powdery mildew and leaf rust responses showed significant associations with genetic diversity, whereas heading date, plant height and yield components did not. Through parallel assessment of genotypic and phenotypic diversity it was possible to separate winter wheat cultivars with similar genotype but diverse phenotype from those with similar phenotype but diverse genotype. This information will allow breeders to make informed decisions in selecting parents for new crosses.