In this study we aimed to explore the significance of glycemic control during gestational diabetes mellitus (GDM) pregnancy in predicting recurrence as this is unknown. A retrospective population-based cohort study of women with first diagnosed GDM pregnancy was conducted. A total of 426 women with 4,226 glucose charts were obtained. Daily glucose values were collected from the glucose charts. Non-parametric (LOWESS) regression was used to present the glucose measurements along the gestational weeks. The analyses revealed that the 2-hour postprandial levels among women with GDM recurrence were substantially higher throughout gestation (PR = 1.89 [95% CI: 1.33, 2.73] for every 20 mg/dl increase). In a multivariable log-binomial regression, the mean postprandial glucose was significantly associated with GDM recurrence (p = 0.017) after adjusting for maternal age, family history of diabetes, insulin use, and inter-pregnancy interval (PR = 1.04 [95% CI: 1.01, 1.07]). The study conclusion is that tighter postprandial glycemic control should be considered. Future studies should explore tighter cutoffs of the 2-hour postprandial glucose.