The association of fluctuations in body mass index with cardiovascular risk in long-term is not well understood. This study aimed to investigate cardiovascular outcomes of weight fluctuation. Total of 67,101 obese adults from the Korean National Health Insurance Service who received health examinations in three separate biennial periods were included. Participants were followed up from January 1, 2008 to the date of cardiovascular disease, death, or December 31, 2015, and categorized into 9 distinctive groups according to the BMI. Continuous weight gain showed an increased risk of overall cardiovascular disease (hazard ratio [HR], 2.36; P = 0.007), whereas weight loss after weight maintenance (HR, 0.91; P = 0.016) and weight maintenance after weight loss (HR, 0.91; P = 0.004) were ameliorative compared to the no weight change group. As for coronary heart disease, weight maintenance after weight gain was unfavorable (HR, 1.25; P = 0.004) while weight loss after weight maintenance (HR, 0.82; P < 0.001), weight cycling (HR, 0.83; P = 0.043), and weight maintenance after weight loss (HR, 0.88; P = 0.012) were beneficial. Weight maintenance after weight loss is beneficial for obese adults in terms of cardiovascular risks. In addition, weight loss is in part related to reduced risk of coronary heart disease despite weight cycling.