Purpose <p>One of a key topic for patients with persistent cloaca is determining when and which procedure to perform vaginoplasty. The purpose of the present study was to clarify the treatment outcomes of simultaneous and metachronous anorecto-vaginoplasty, and to define limit for timing of simultaneous surgery.</p> Methods <p>The present study was retrospective cohort study reviewed based on the results of a national survey in Japan. A total of 299 patients underwent both vaginoplasty and anorectoplasty were enrolled in the present study. We compared patient characteristics, surgical outcomes, and menstrual related surgical outcomes between the simultaneous (n=237) and metachronous surgery (n=62) groups.</p> Results <p>The median follow-up term after vaginoplasty of all patients was 144 [77-223] months. The ages at the first redo-vaginoplasty and anorectoplasty were significantly younger in the simultaneous group than in metachronous surgery group (<i>p</i>=&lt; 0.01). The incidence of surgical management for menstrual outflow obstruction showed a lower trend in the simultaneous surgery group (<i>p</i>=0.08). The cutoff surgical timing based on defecation function in the simultaneous surgery group was 18 months (<i>p</i>=&lt; 0.01).</p> Conclusions <p>Simultaneous surgery can be comparably feasible to metachronous surgery without increasing the need for redo-vaginoplasty or redo-anorectoplasty.</p>