Background: Understanding the drivers contributing to the decreasing trend in stunting is paramount to meeting the World Health Assembly’s global target of 40% stunting reduction by 2025. Methods: We pooled data from 50 Demographic and Health Surveys since 2000 in 14 countries to examine the relationships between the stunting trend and potential factors at distal, intermediate, and proximal levels. A multilevel pooled trend analysis was used to estimate the association between the change in potential drivers at a country level and stunting probability for an individual child while adjusting for time trends and child-level covariates. A four-level mixed-effects linear probability regression model was fitted, accounting for the clustering of data by sampling clusters, survey-rounds, and countries. Results: Stunting followed a decreasing trend in all countries at an average annual rate of 1.04 percentage points. Among the distal factors assessed, a decrease in the Gini coefficient, an improvement in women’s decision-making, and an increase in urbanization were significantly associated with a lower probability of stunting within a country. Improvements in households’ access to improved sanitation facilities and drinking water sources, and children’s access to basic vaccinations were the important intermediate service-related drivers, whereas improvements in early initiation of breastfeeding and a decrease in the prevalence of low birthweight were the important proximal drivers. Conclusions: The results reinforce the need for a combination of nutrition-sensitive and -specific interventions to tackle the problem of stunting. The identified drivers help to guide global efforts to further accelerate stunting reduction and monitor progress against chronic childhood undernutrition.