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Abstract Aims/Introduction We investigated the difference in efficacy and safety between discontinuation and maintaining of sulfonylurea when adding a sodium–glucose cotransporter 2 inhibitor. Materials and Methods In the present multicenter, prospective observational study, 200 patients with type 2 diabetes treated with sulfonylurea and with a need to add ipragliflozin were enrolled and divided into two groups: discontinued sulfonylurea (Discontinuation group) or maintained sulfonylurea, but at the lowest dose (Low‐dose group) when adding ipragliflozin. We compared the two groups after 24 weeks using propensity score matching to adjust for differences between the groups. Results In the matched cohort (58 patients in each group), baseline characteristics of both groups were balanced. The primary outcome of the proportion of patients with non‐exacerbation in glycated hemoglobin after 24 weeks was 91.4% in the Low‐dose group and 75.9% in the Discontinuation group, a significant difference (P = 0.024). However, bodyweight was significantly decreased in the Discontinuation group compared with the Low‐dose group (−4.4 ± 2.1 kg vs −2.9 ± 1.9 kg, P