Optimal breastfeeding practices, including early initiation of breastfeeding (EIBF) within 1 hr of birth, exclusive breastfeeding (EBF) for the first 6 months of age, and continued breastfeeding (CBF) for 2 years of age or beyond with appropriate complementary foods, are essential for child survival, growth, and development. Breastfeeding norms differ within and between countries in South Asia, and evidence is needed to inform actions to protect, promote, and support optimal practices. This study examines time trends and predictors of EIBF, avoidance of prelacteal feeding (APF), EBF, and CBF to 2 years using survey data from Afghanistan, Bangladesh, India, Nepal, and Pakistan since 1990. EIBF, APF, and EBF increased in Bangladesh, India, and Nepal from 1990 to 2016. EIBF and EBF increased in Pakistan from 1990 to 2013, but both EIBF and APF decreased in recent years. In Afghanistan, EIBF, APF, and EBF decreased from 2010 to 2015. CBF remained fairly constant across the region although prevalence varied by country. Significant (
p
< 0.05) predictors of suboptimal practices included caesarian delivery (4–25%), home delivery, small size at birth, and low women's empowerment. Wealth, ethnic group, and caste had varied associations with breastfeeding. Progress towards optimal breastfeeding practices is uneven across the region and is of particular concern in Afghanistan and Pakistan. There are some common predictors of breastfeeding practices across the region, however country‐specific predictors also exist. Policies, programs, and research should focus on improving breastfeeding in the context of women's low empowerment and strategies to support breastfeeding of infants born small or by caesarian section, in addition to country‐specific actions.