Anticoagulant therapy is essential in pregnant women with mechanical heart valves to prevent valve thrombosis. The risk of bleeding complications in these patients has not gained much attention. This systematic review and meta-analysis investigate the prevalence of bleeding peri-partum and post-partum in women with mechanical heart valves and also investigate whether bleeding risk differed across anticoagulant regimens or according to delivery mode. The present study was conducted according to The Preferred Reporting Items for Systematic reviews and Meta-Analyses (PRISMA) statement. Studies reporting bleeding prevalence in pregnant women with mechanical heart valves receiving anticoagulant therapy were identified through PubMed and Embase on December 08, 2021. Data on bleeding complications, delivery mode, and anticoagulation therapy were extracted. A total of 37 studies were included, reporting 423 bleeding complications in 2,508 pregnancies. A meta-analysis calculated a pooled prevalence of 0.13 (95% confidence interval [CI]: 0.09–0.18) bleeding episodes per pregnancy across anticoagulant regimens. The combination of unfractionated heparin (UFH) and vitamin K antagonist (VKA) and single VKA therapy showed the lowest risk of bleeding (8 and 12%). Unexpectedly, the highest risk of bleeding was found in women receiving a combination of low-molecular-weight-heparin (LMWH) and VKA (33%) or mono-therapy with LMWH (22%). However, this could be dose related. No difference in bleeding was found between caesarean section versus vaginal delivery (p = 0.08). In conclusion, bleeding episodes are common during pregnancy in women with mechanical heart valves receiving anticoagulant therapy. A combination of UFH and VKA or VKA monotherapy showed the lowest risk of bleeding.