The present study investigates the twinning rates in the city of São Paulo, Brazil, during the years 2003–2014. The data were drawn from the Brazilian Health Department database of Sistema de Informações de Nascidos Vivos de São Paulo—SINASC (Live Births Information System of São Paulo). In general, more information is available on the incidence of twinning in developed countries than in developing ones. A total of 24,589 twin deliveries and 736 multiple deliveries were registered in 140 hospitals of São Paulo out of a total of 2,056,016 deliveries during the studied time period. The overall average rates of singleton, twin, and multiple births per 1,000 maternities (‰) were 987.43, 11.96 (dizygotic (DZ) rate was 7.15 and monozygotic (MZ) 4.42), and 0.36, respectively. We further regressed maternal age and historical time period on percentage of singleton, twin, and multiple birth rates. Our results indicated that maternal age strongly positively predicted twin and multiple birth rates, and negatively predicted singleton birth rates. The historical time period also positively, although weakly, predicted twin birth rates, and had no effect on singleton or multiple birth rates. Further, after applying Weinberg's differential method, we computed regressions separately for the estimated frequencies of DZ and MZ twin rates. DZ twinning was strongly positively predicted by maternal age and, to a smaller degree, by time period, while MZ twinning increased marginally only with higher maternal age. Factors such as increasing body mass index or air pollution can lead to the slight historical increase in DZ twinning rates. Importantly, consistent with previous cross-cultural and historical research, our results support the existence of an age-dependent physiological mechanism that leads to a strong increase in twinning and multiple births, but not singleton births, among mothers of higher age categories. From the ultimate perspective, twinning and multiple births in later age can lead to higher individual reproductive success near the end of the reproductive career of the mother.