Anise, Pimpinella anisum, is a flowering plant of high phytoestrogen content and medicinal properties. The systematic review and meta-analysis aimed to investigate the influence of anise and anise-containing supplements on gynecological complaints. An online search was conducted up to August 2024 on Google Scholar, Scopus, Cochrane Library, and PubMed. Studies were assessed using the Cochrane Risk of Bias 2 tool and GRADE for certainty of evidence. Meta-analysis was done using risk ratio (RR) and mean difference (MD), respectively, with a 95% confidence interval (CI). Eight randomized controlled trials evaluating the effect of anise on gynecological symptoms in 566 women, both menopausal and non-menopausal, were included. Regular menstruation occurred more frequently in oligomenorrheic polycystic ovarian syndrome patients treated with anise-containing supplement than with metformin (RR = 2.31, 95% CI [1.35, 3.96]). In primary dysmenorrhea, pain scores decreased in the anise-containing supplement group compared to placebo (MD = -5.78, 95% CI [-6.27, -5.28]) and premenstrual tension syndrome symptoms improved. In menopausal women, anise decreased the frequency of hot flashes (MD = -2.78, 95% CI [-3.84, -1.72]) with hot flashes less likely to be severe (RR = 0.07, 95% CI [0.01, 0.49]). Sexual dysfunction and constipation were reduced in postmenopausal women. Anise’s safety profile was favorable, but vaginal spotting in menopausal women warrants further investigation. The quality of the studies and certainty of evidence varied. There is compelling evidence for further pharmaceutical exploration of anise as a gynecological supplement. Larger, higher quality randomized controlled trials are needed to confirm these findings.