The impact of Bariatric Surgery (BS) on maternal and neonatal outcomes among pregnant women is not fully understood, especially in comparison to different weight categories. The primary aim of this study is to assess the factors associated to women who have undergone BS. The study also investigates the maternal and neonatal outcomes amongst this group in comparison to the three Body Mass Index (BMI) groups (women with obesity, overweight and normal weight). A 12-month population-based retrospective study was conducted using registry data from the PEARL-Peristat Study at the Women's Wellness and Research Center (WWRC) in Qatar from January 1, 2017, through December 31, 2017. Both univariate and multivariable regression analyses were employed to scrutinize risk factors and maternal and neonatal outcomes. The study included 6212 parturient women, of which 315 had a history of BS, while 5897 with no BS history. Qatari women, aged 35 and higher, with parity > 1, diabetes, and hypertension were more likely to be in the post-BS group. Women in the post-BS group were found to be more likely to have a cesarean delivery (37.5% vs. 24%, Adjusted Odds Ratio (aOR) = 1.59, CI 1.18–2.14), preterm babies (10% vs. 7%, aOR = 1.66, CI 1.06–2.59), and stillbirth (1.6% vs. 0.4%, aOR = 4.53, CI 1.33–15.50) compared to the normal weight women group. Moreover, post-BS women had a higher risk of low-birth-weight neonates than women with obesity (15% vs. 8%, aOR = 1.77, CI 1.153–2.73), overweight (15% vs. 7%, aOR = 1.63, CI 1.09–2.43), and normal weight (15% vs. 8%, aOR = 1.838, CI 1.23–2.75). Finally, women in the post-BS group were more likely to have low-birth-weight neonates amongst term babies than women with obesity and overweight. Pregnancies with post-BS should be considered a high-risk group for certain medical outcomes and should be monitored closely. These findings may guide the future clinical decisions of antenatal and postnatal follow-up for post-BS women.