Background : The menstrual irregularity cycle mostly happen on teenage girl. Stress was the most influence on the menstrual irregularity cycle. The stress trigger on collage girls happend when they face a lot assignment and the extracuricullar activity such as islamic boarding school. Purpose : To know the correlation between the level of stress with menstrual cycle at Pondok Pesantren Al Munawwir Komplek R2 Krapyak Method : This research used non eksperiment research with cross sectional approach. The population of this research was female students of Pondok Pesantren Al Munawwir Komplek R2 Krapyak by the number was 180 people. Sampling used was a non probability sampling method with random sampling technique andobtained the sample of 131 people. This study used 2 questionnaires, namely the menstrual cycle calender and Student Life Stress Inventory (SLSI) questionnaire. Univariate analysis is aiming to describing every research of variable characteristics, for a while bivariate analysis is aiming to explain the correlation between dependent vaiable and independent variable used Chi-Square test. Results : At the end of study it was found that 59 respondents (51,5%) got moderate stress with normal menstrual cycle and 31 respondents (38,5%) got moderate stress with not normal menstrual cycles. By scores p = 0,004 ( p <0,05). Conclusion : There is a significant correlation between the level of stress with menstrual cycle at Pondok Pesantren Al Munawwir Komplek R2 Krapyak