The genus Cladonia is widely distributed around the world. Since the section Cladonia contains species complexes that are difficult to distinguish, the distributions of species within these complexes are even less well-known than others. The cup-forming species, Cladonia magyarica, is morphologically similar to C. pyxidata and C. pocillum; and C. humilis is morphologically similar to C. conista and C. chlorophaea. Both species, C. magyarica and C. humilis, have not been previously reported for Manitoba, but their distribution ranges fall very close to the province, and they grow in habitats that are present in southern Manitoba. The goal of this paper was to report the presence of C. magyarica and C. humilis in Manitoba representing range extensions for both species, and to show morphological differences among them and their close allies present in the same geographic locations. The morphological differences between C. magyarica and C. pyxidata include squamules inside the cup and a significantly taller podetium and wider cup diameter in C. magyarica than C. pyxidata. Cladonia magyarica also differs from C. pyxidata in possessing atranorin in addition to fumarprotocetraric acid, in every specimen we collected. Atranorin and fumarprotocetraric acid were also shown to be present in C. humilis, but C. humilis has soredia covering the podetium, which is not present in the aforementioned taxa.