Different moderators/mediators of risk are involved in developmental dyslexia (DD), but data are inconsistent. We explored the prevalence of season of birth and its association with gender and age of school entry in an Italian sample of dyslexic children compared to an Italian normal control group. The clinical sample included 498 children (345 boys, mean age 10.3 ± 2.1 years) with DD, the control sample 1,276 children (658 boys, mean age 10.8 ± 2.2 years) from four elementary schools from the same urban area, and with the same socio-economic status level. A prevalence of birth in autumn was found among children with DD compared to controls (34% versus 24%, p < 0.0001). Children with DD were more frequently males (p < 0.0001) and had a lower mean age of school entry (p < 0.0001). Regarding the distribution of ages, 11.4% of children with DD, but none of the subjects in the control group, started school before 5.7 years. Therefore, greater risk of DD was related to age of school entry (OR = 2.72), gender (OR = 2.16), and season of birth (OR = 1.21). Significant interactions between boys with DD born in autumn, and correct school of entry (OR = 2.56) were joint predictors of higher risk of DD. The association between birth in autumn and DD may be explained by the earlier age of school entry, which may be a critical element in the youngest children with DD or at risk to DD. Whether Italian school policy is oriented to anticipate the school entry, a closer detection of early learning disorders and associated risk factors (familial load, specific language disorders, and attention deficit hyperactivity disorder) should be warranted.