Background andObjectives: This study aimed to determine the correlation between maternal weight gain in each trimester and fetal growth according to pre-pregnancy maternal body mass index in twin pregnancies. Materials and Methods: We conducted a retrospective review of the medical records of 500 twin pregnancies delivered at 28 weeks’ gestation or greater at a single tertiary center between January 2011 and December 2020. We measured the height, pre-pregnant body weight, and maternal body weight of women with twin pregnancies and evaluated the relationship between the maternal weight gain at each trimester and fetal growth restriction according to pre-pregnancy body mass index. Results: The overweight pregnant women were older than the normal or underweight pregnant women, and the risk of gestational diabetes was higher. The underweight pregnant women were younger, and the incidence of preterm labor and short cervical length during pregnancy was higher in the younger group. In normal weight pregnant women, newborn babies’ weight was heavier when their mothers gained weight, especially when they gained weight in the second trimester. Mothers’ weight gain in the first trimester was not a significant factor to predict fetal growth. The most predictive single factor for the prediction of small neonates was weight gain during 24–28 and 15–18 weeks, and the cutoff value was 6.2 kg (area under the curve 0.592, p < 0.001). Conclusions: In twin pregnancy, regardless of the pre-pregnant body mass index, maternal weight gain affected fetal growth. Furthermore, weight gain in the second trimester of pregnancy is considered a powerful indicator of fetal growth, especially in normal weight pregnancies.