Alpha lipoic acid (ALA) is a naturally occurring micronutrient with potent antioxidant and anti-inflammatory activities. For these characteristics, ALA dietary supplementation has been suggested in pregnancy with the aim of reducing the risk of adverse pregnancy outcomes in cases associated with the effects of inflammation and/or oxidative stress. In this review, we synthesize evidence for the uses of ALA in recurrent pregnancy loss (RPL), threatened miscarriage, preterm birth, and gestational diabetes, showing both the results of clinical trials and animal/in-vitro studies. Our opinion, based on the current knowledge, suggests that ALA may reduce paternal sperm DNA fragmentation and maternal endometrial inflammation in cases with a high risk of RPL and may improve the resorption of subchorionic hematoma in threatened miscarriage. ALA is also promising in helping cervical length in women at high risk for preterm delivery and in improving glucose and lipid metabolism in gestational diabetes. Although the current evidence about ALA supplementation in human pregnancy is preliminary, the available studies encourage planning further powered randomized controlled clinical trials aimed at confirming these promising effects, with the ambitious aim of improving pregnancy outcomes in high-risk conditions.