Wellbeing has recently been given a more prominent place in education policy and discourse, with critics arguing that an overemphasis on achievement comes at the cost of well-being. This raises questions concerning possible trade-offs between the traditionally dominant focus on learning and achievement in education and the growing emphasis on well-being. Can education systems promote high achievements and wellbeing simultaneously, or is reduced wellbeing an inevitable price to pay for high academic achievements? In this study, I investigate possible trade-offs between country-level achievement and individual wellbeing using five waves of the Programme for International Student Assessment (PISA) and the Health Behaviour in School-aged Children (HBSC) data, spanning over 18 years and including more than one million pupils in 45 countries. I find weak and inconsistent empirical support for a trade-off. While there is a modest negative relationship between country-level achievement and some indicators of well-being, this does not hold when adjusting for possible confounders or country-fixed effects. I also find no or weak evidence for heterogeneous effects depending on individual achievement. I conclude that concerns regarding possible trade-offs between achievement and wellbeing are not supported by cross-country comparative data. However, the predominantly null findings also imply that policymakers should not expect miracles in terms of wellbeing from high-achieving education systems. High achievements may be good from an academic perspective, but do not seem to make much of a difference from the perspective of wellbeing.