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Objective: To compare the treatment strategies and pregnancy outcomes between women with gestational diabetes mellitus carrying twin and singleton pregnancies. Method: We conducted a retrospective chart review of women with singleton and twin pregnancy; those visited Sunil's Diabetes Care n' Research Centre, Nagpur, and Gupte Hospital Pune, between 2006 and 2019, for the treatment of gestational diabetes mellitus (GDM). Propensity scores for baseline characteristics were used to assemble a matched-pairs cohort of women with twin and singleton pregnancies. Results: A subset of 132 singleton cases was obtained from 801 records that matched with 44 cases of twin pregnancy, with a ratio of 3:1. Treatment modalities, insulin dose, and mode of delivery differed insignificantly between the two groups. Univariate analysis showed significantly higher risk of Premature Baby Unit (PBU) admission > 48 h (OR 2.687; 95% CI 1.064–6.784; p = 0.0364) and small for gestational age newborns (OR 5.286; 95% CI 2.826–9.887; p < 0.0001) in twin pregnancies, and lower risk of premature birth (OR 0.225; 95% CI 0.127–0.402; p < 0.0001) and large for gestational age newborns (OR 0.239; 95% CI 0.068–0.841; p < 0.0257). In a multiple regression analysis, twin pregnancies were found to be the strongest predictors of small for gestational age infant (OR 3.960; 95% CI 1.928–8.135; p < 0.0001). Conclusion: Although treatment strategies and insulin doses differ insignificantly between gestational diabetes mellitus women carrying twin and singleton pregnancies, their treatment should be planned to achieve glycemic goals. [ABSTRACT FROM AUTHOR]