The main objective of the study is to develop and test a model that emphasizes the relationship between entrepreneurial orientation (EO) and managerial capacity (MC) to the performance of dairy farms. This article also examines the effect of these variables on performance expectations as well as the succession planning of farms. Cross-sectional data were collected out of a sample of 158 dairy farmers in 2017 in Brazil. A path analysis approach has been applied to validate the hypothesized model. Results show that between EO dimensions, innovativity has the greatest impact on performance as well as on MC. MC is not significantly related to the current performance on dairy farms, but it is so to the performance expectation, which in turn has an impact on the succession planning of farms. The age of the farmers moderates the relations hypothesized in the model, especially between innovativity, proactivity, and MC in the farms’ performance.