This study examined how parents supported children's writing and math and whether parents' support predicted children's academic skills from the beginning of pre-kindergarten to the end of kindergarten. Two hundred ten Chilean parents from low-income households were observed playing a grocery game with their preschoolers (M = 53 months). The grocery game (a game where dyads make a grocery list together and shop at a pretend store) could be used to foster writing and mathematics. Coders noted how often parents engaged in writing support, provided math support, and displayed directiveness (i.e., taking over the child's activity). Children's literacy and math skills were assessed at the beginning of pre-kindergarten and the end of kindergarten. Research Findings. Parents engaged in little writing support but displayed moderate levels of math support and high levels of directiveness in the grocery game. Parents' math support uniquely predicted gains in children's math skills, while parents' directiveness negatively predicted gains in children's literacy skills. Practice or Policy. Results from this study have the potential to inform parent-focused interventions. Findings highlight the need to provide parents with specific strategies to support their children's literacy and math development and guidance about embedding these strategies into family routines.