Female workers in entertainment venues are at higher risk of experiencing reproductive health problems due to shift work patterns, lack of rest, exposure to cigarette smoke, and unhealthy diets. This study aimed to analyze the relationship between menstrual cycles and anemia status with the risk of PCOS in female billiard workers in Samarinda City. The study used an observational analytical design with a cross-sectional approach. The study sample consisted of 96 subjects selected using simple random sampling. Data were collected through closed questionnaires and hemoglobin level examinations. Data analysis was performed univariately and bivariately using the Chi-Square test with a 95% confidence level and the strength of the association with the PR value. The results showed that the majority of subjects experienced irregular menstrual cycles (54%) and anemia (76%). Subjects at risk of PCOS were 39.6%. There was a significant association between anemia status and PCOS risk (p = 0.045; PR = 2.08), meaning that subjects with anemia had a 2.08-fold higher prevalence of PCOS risk. In addition, irregular menstrual cycles were also significantly associated with the risk of PCOS (p = 0.001; PR = 3.75). Irregular menstrual cycles were associated with a 3.75-fold higher prevalence of PCOS risk than regular menstrual cycles. This study concluded that menstrual cycle and anemia status are factors associated with PCOS risk in female billiard workers. Reproductive health education, monthly menstrual cycle monitoring, and routine Hb level checks are needed as an effort for early detection and prevention of PCOS in women of reproductive age.