Polycystic ovary syndrome (PCOS) is a common metabolic problem in women of reproductive age. Evidence suggests pregnant women with PCOS may have a higher risk of the development of adverse pregnancy outcomes; however, the relationship between pre-pregnancy overweight/obesity and pregnancy outcomes in women with PCOS remains uncertain. We try to clarify the relationship between pre-pregnancy overweight/obesity and subsequent pregnancy outcomes. Therefore, we conducted this systematic review and meta-analysis. We used the databases obtained from the PubMed, Embase, Web of Science, and Cochrane databases, plus hand-searching, to examine the association between pre-pregnancy overweightness/obesity and pregnancy outcomes in women with PCOS from inception to 4 February 2022. A total of 16 cohort studies, including 14 retrospective cohort studies (n = 10,496) and another two prospective cohort studies (n = 818), contributed to a total of 11,314 women for analysis. The meta-analysis showed significantly increased odds of miscarriage rate in PCOS women whose pre-pregnancy body mass index (BMI) is above overweight (OR 1.71 [95% CI 1.38–2.11]) or obese (OR 2.00 [95% CI 1.38–2.90]) under a random effect model. The tests for subgroup difference indicated the increased risk was consistent, regardless which body mass index cut-off for overweight (24 or 25 kg/m2) or obesity (28 and 30 kg/m2) was used. With the same strategies, we found that pregnant women in the control group significantly increased live birth rate compared with those pregnant women with PCOS as well as pre-pregnancy overweight/obesity (OR 0.79 [95% CI 0.71–0.89], OR 0.78 [95% CI 0.67–0.91]). By contrast, we did not find any association between PCOS women with pre-pregnancy overweight/obesity and preterm birth. Based on the aforementioned findings, the main critical factor contributing to a worse pregnancy outcome may be an early fetal loss in these PCOS women with pre-pregnancy overweight/obesity. Since PCOS women with pre-pregnancy overweightness/obesity were associated with worse pregnancy outcomes, we supposed that weight reduction before attempting pregnancy in the PCOS women with pre-pregnancy overweightness/obesity may improve the subsequent pregnancy outcomes.