Portulaca grandiflora Hook and P. umbraticola Kunth (Portulacaceae) are popular garden annuals, and have been bred for improved ornamental value. However, limited research has been published on hybridisation of Portulaca, with no reports on intergeneric hybridisation. Calandrinia balonensis Lindley and Calandrinia sp. nov. (not yet fully classified) are floriferous Australian Portulacaceae species, with potential as novel flowering pot plants, and are potential candidates for breeding with ornamental Portulaca. We studied the reproductive biology of these four species and breeding compatibility for reciprocal crosses of P. grandiflora × C. balonensis (2n = 18) and P. umbraticola × C. sp. nov. (2n = 24). All four species produced seeds for intraspecific outcrosses. P. grandiflora and C. sp. nov. are partially self-compatible whereas P. umbraticola and C. balonensis are highly self-incompatible. Autogamy was detected only for P. grandiflora. Reciprocal crosses of P. grandiflora × C. balonensis and P. umbraticola × C. sp. nov. with similar chromosome numbers did not produce seeds, primarily because of pollen–pistil incompatibility that prevents pollen-tube growth within the stigmata. Methods to overcome hybridisation barriers of these species combinations need to be established to create novel products for ornamental horticulture.