(1) Background: Women with personality disorder are at risk of social and emotional problems which impact deleteriously on everyday functioning. Moreover, a personality disorder diagnosis has been established to have an adverse impact upon pregnancy outcomes and child health. Understanding this impact is critical to improving both maternal and child outcomes. This systematic review and meta-analysis will evaluate the contemporary evidence regarding these relationships. (2) Methods: Prospero and Cochrane were searched for any systematic reviews already completed on this topic. Academic Search Premier, CINAHL Complete, MEDLINE, PsycARTICLES, PsycINFO via the EBSCO host, and the Web of Science Core Collection were searched to include research articles published between 1980 and 2019. A total of 158 records were identified; 105 records were screened by reviewing the abstract; 99 records were excluded; 6 full text articles were assessed for eligibility; 5 records were included in the review. (3) Results: All the included studies reported on preterm birth. The meta-analysis indicates significant risk of preterm birth in women with personality disorder (overall odds ratio (OR) 2.62; CI 2.24–3.06; p < 0.01). Three studies reported on low birth weight, with the meta-analysis indicating a raised risk of low birth weight of the babies born to women with personality disorder (overall OR 2.00 CI 1.12–3.57 (p = 0.02)). Three studies reported on appearance, pulse, grimace, activity, and respiration (APGAR) score, with the meta-analysis of OR’s indicating a risk of low APGAR score in women with personality disorder (overall OR 2.31; CI 1.17–4.55; p = 0.02). (4) Conclusions: The infants of women with personality disorder are at elevated risk of preterm birth, low birth weight and low APGAR score.