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School dropout has well-documented deleterious effects, including social, economic, and personal consequences (Pica et al., 2014). Academic performance has been associated with school persistence and later adult functioning, namely education level, income and social inclusion (Doll et al., 2013; Feinstein & Bynner, 2004). Hence, it is important to identify early malleable factors that can promote academic performance and thus school persistence. Among possible factors, maternal autonomy support could play a role in academic performance by promoting intrinsic motivation and executive functions (Bindman et al., 2015; Grolnick et al., 1991). Maternal autonomy support involves encouraging children to solve problems on their own and to be self-initiating rather than pressuring them to behave in certain ways. Several studies have found positive associations between maternal autonomy support and child academic achievement (Vasquez et al., 2015). However, few studies examining these constructs have assessed academic performance more than once or assessed maternal autonomy support objectively, by observation. The present study aimed to investigate the effects of observationally assessed maternal autonomy support on the developmental trajectories of early school performance, specifically mathematics skills. 121 mother-child dyads (54 boys) participated in four home visits. Maternal autonomy support was assessed at 15 months. Videotaped mother—infant interactions consisting of three joint problem-solving tasks (10 minutes) were coded following Whipple et al.’s (2010) coding system (interrater agreement: ICC = .96). When children were in first, second and third grade of elementary school, their mathematics skills were assessed using the Weschler Individual Assessment Test (Weschler, 2005). In order to examine intraindividual patterns of change in mathematics skills, multilevel growth models were estimated using Mplus (Muthén & Muthén, 1998–2012). Results revealed significant improvement in mathematics skills between first and third grades (b = 6.68, p < .001). Maternal autonomy support was marginally associated with the rate of change in mathematics skills (b = .54, p = .053), above and beyond family socioeconomic status. Maternal autonomy support was also significantly associated with third-grade mathematics skills’ level (b = 2.19, p = .003). These findings suggest that maternal autonomy support in infancy may play a role in growth patterns of academic performance at a critical time, namely when children begin elementary school. Maternal autonomy support was related to more pronounced yearly growth in mathematics skills (marginally). Furthermore, it was associated with higher mathematics skills, nearly 8 years later. This suggests that maternal autonomy support may foster abilities in children that promote learning (e.g., motivation, task engagement), and thus, the rate at which children acquire new skills in elementary school. These results highlight the importance of studying academic performance longitudinally and at different time points as parenting might affect children’s achievement trajectories, which cannot be studied cross-sectionally.