ABSTRACT Tomato genotypes ( Solanum spp.) have genetic variability of most desirable features, such as resistance to biotic and abiotic stresses. However, incompatibility of crosses of wild genotypes with domesticated tomatoes, or even between wild genotypes, hinders the breeding process. Thus, knowledge of the reproductive biology of genotypes and conditions is necessary to maximize the success of artificial crossings. This study evaluated the compatibility of self-pollination, intra- and interspecific controlled crosses, stigma receptivity, and pollen viability in tomato genotypes. We used two commercial genotypes S. lycopersicum (‘RVTM08’ and ‘Redenção’) and seven accessions of wild tomato genotypes (‘AF 26970’, ‘LA-1401’, ‘AF 19684’, ‘LA-1967’, ‘PI-127826’, ‘PI-134417’, and ‘LA-716’). We evaluated all crosses and their reciprocals, besides the self-pollinations. The variables evaluated were fruit index (FI), number of seeds per fruit (SN), and seed germination percentage (GP). Stigma receptivity and grains’ pollen viability index (PVI) were also assessed. The results showed that ‘LA-1967’ was self-incompatible, had a low PVI, and generated fruit without seeds in most crosses. As female parents, ‘RVTM08’, ‘Redenção’, ‘AF 26970’, ‘LA-1401’, and ‘AF 19684’ showed higher FI and SN. There was a wide diversity of reproductive characteristics between the genotypes and crosses that did not influence GP. Compatibility of crosses in tomatoes is determined by the female parent choice and can be affected by stigma receptivity and the PVI.