A Syrian grassland was subject to 13 years of replicated management treatments, namely a factorial design of 0 or 60 kg/ha annually of phosphate fertilizer, combined with relatively low or high sheep stocking intensities. Previous work found that differences in grazing intensity and phosphate induced changes in the structure of the legume community, presumably due to changes in competitive relationships. The aim of this study was to investigate how the populations of the predominant clover species, Trifolium campestre and Trifolium tomentosum, changed as a consequence of management treatments. We hypothesized that the populations from the fertilized or low grazing intensity treatments would express phenotypic traits associated with increased competitive ability and/or with risk mitigation. Populations of both ruderal-type clover species provided evidence of evolution but were largely responsive to different management factors. Assuming that heavy grazing and no fertilizer are the natural state of the grassland, addition of phosphate led to T. tomentosum plants that were wider and had larger seeds, traits associated with improved competitive ability. The populations from the fertilized paddocks had increased fecundity and a trend towards greater dormancy, traits associated with risk mitigation. In contrast, T. campestre plants became wider and more erect when stocking intensities were reduced and had greater seed dormancy in fertilized paddocks. The implication of this work is that the collection of germplasm from grasslands with a history of heavy grazing and fertilizer application may assist agronomists to find genotypes that are better adapted to pastures within ley farming systems in Australia.