According to national survey data, dairy food consumption has fallen in recent years and declines further with age, especially from childhood to adolescence. Dietary surveys typically rely on retrospective dietary assessment methods and use broad age groupings (4–10 yr; 11–18 yr), making it challenging to differentiate between middle-childhood and adolescence. Consequently, there is a need to assess dairy food consumption during middle-childhood and adolescence using more robust dietary assessment tools. Therefore, the present study aimed to describe and compare patterns of dairy consumption throughout middle-childhood and adolescence. Dairy food consumption was assessed during school term-time over 4 consecutive days, including 2 weekdays and 2 weekend days, in a sample of free-living children (9–11 yr, n = 40) and adolescents (15–18 yr, n = 35). For children, free-living dairy intake was evaluated through parental-weighed food records, and for adolescents, a combined weighed self-reported food record and 24-h dietary recall technique was utilized. Food records were explored to determine types, amounts, and frequency of dairy food consumption, and were analyzed for differences between middle-childhood and adolescence using a between group 2 × 2 (age × sex) ANOVA. Descriptive data suggested that milk was the most popular dairy product consumed by both children and adolescents. Statistical analysis revealed a main effect for sex on total milk consumption (mL) and number of daily milk portions consumed. No interaction or main effect was present for any other variable. The present study indicates that independent of age, boys consumed greater amounts of milk compared with girls. Contrary to existing literature, findings suggest no difference in milk-based dairy consumption between middle-childhood and adolescence.